3-Pyridineacetic acid, hydrochloride (1:1) → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-(2-(pyridin-3-yl)acetamido)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

HRID 85605

Reaction equation

HRID 85605 reaction equation
[NH2:1][C@:2]12[CH2:37][CH2:36][C@@H:35]([C:38]([CH3:40])=[CH2:39])[C@@H:3]1[C@@H:4]1[C@@:17]([CH3:20])([CH2:18][CH2:19]2)[C@@:16]2([CH3:21])[C@@H:7]([C@:8]3([CH3:34])[C@@H:13]([CH2:14][CH2:15]2)[C:12]([CH3:23])([CH3:22])[C:11]([C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=2)=[CH:10][CH2:9]3)[CH2:6][CH2:5]1.Cl.[N:42]1[CH:47]=[CH:46][CH:45]=[C:44]([CH2:48][C:49](O)=[O:50])[CH:43]=1>>[CH3:20][C@:17]12[C@@:16]3([CH3:21])[C@@H:7]([C@:8]4([CH3:34])[C@@H:13]([CH2:14][CH2:15]3)[C:12]([CH3:23])([CH3:22])[C:11]([C:24]3[CH:33]=[CH:32][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=3)=[CH:10][CH2:9]4)[CH2:6][CH2:5][C@@H:4]1[C@H:3]1[C@H:35]([C:38]([CH3:40])=[CH2:39])[CH2:36][CH2:37][C@:2]1([NH:1][C:49](=[O:50])[CH2:48][C:44]1[CH:43]=[N:42][CH:47]=[CH:46][CH:45]=1)[CH2:19][CH2:18]2

Participants

3

Reactant 2

HCID 27237243-Pyridineacetic acid, hydrochloride (1:1)HCID 68357865methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

Product 1

HCID 683580424-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-(2-(pyridin-3-yl)acetamido)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

Procedure

The title compound was prepared from methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate following the general procedure described for the parallel synthesis of C-17 amides above, using 3-pyridylacetic acid hydrochloride as the reacting carboxylic acid. LCMS: m/e 649.6 (M+H)+, 4.07 min (method 3). 1H NMR (599 MHz, <DMSO_CDCl3>) δ=8.49 (d, J=5.3 Hz, 2H), 7.88 (s, 2H), 7.33 (d, J=5.3 Hz, 2H), 7.22 (d, J=8.2 Hz, 2H), 7.17 (s, 1H), 5.28 (d, J=5.3 Hz, 1H), 4.86-4.81 (m, 1H), 4.76 (s, 1H), 4.63 (br. s., 1H), 3.66 (d, J=12.9 Hz, 1H), 3.49 (d, J=12.9 Hz, 1H), 2.85-2.79 (m, 1H), 2.60-2.56 (m, 1H), 2.35-2.28 (m, 1H), 2.12 (dd, J=6.4, 17.0 Hz, 1H), 2.06 (t, J=11.1 Hz, 1H), 1.87-1.79 (m, 1H), 1.73 (br. s., 2H), 1.71 (s, 3H), 1.61-1.50 (m, 2H), 1.50-1.35 (m, 6H), 1.37-1.27 (m, 3H), 1.24 (d, J=9.4 Hz, 3H), 1.13-1.05 (m, J=12.9 Hz, 1H), 1.03-1.00 (m, 6H), 0.97 (s, 3H), 0.94 (s, 3H), 0.93 (s, 3H).

Workup

  1. customm/e 649.6 (M+H)+, 4.07 min (method 3)

Sources & evidence

ORD record
ord-4e22e6d696f1486182e79f65af8fdca3
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Linked notes

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