Trifluoroacetic acid → HCID 71611309, compound

HRID 524466Notes

Reaction equation

HRID 524466 reaction equation
[CH3:1][C:2]([CH3:59])([CH2:10][C:11]([O:13][C@H:14]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@@H:16]([CH2:17][CH2:18][C@:19]3([CH3:56])[C@@H:28]2[CH2:27][CH2:26][C@H:25]2[C@@:20]3([CH3:55])[CH2:21][CH2:22][C@@:23]3(/[CH:40]=[CH:41]/[C:42]([NH:44][C:45]4([C:48]5[N:53]=[CH:52][C:51]([Cl:54])=[CH:50][N:49]=5)[CH2:47][CH2:46]4)=[O:43])[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[C:24]32)[C:15]1([CH3:58])[CH3:57])=[O:12])[C:3]([O:5]C(C)(C)C)=[O:4].C(O)(C(F)(F)F)=O>ClCCl>[Cl:54][C:51]1[CH:52]=[N:53][C:48]([C:45]2([NH:44][C:42](=[O:43])/[CH:41]=[CH:40]/[C@:23]34[CH2:35][C:34](=[O:36])[C:33]([CH:37]([CH3:38])[CH3:39])=[C:24]3[C@@H:25]3[C@@:20]([CH3:55])([CH2:21][CH2:22]4)[C@@:19]4([CH3:56])[C@@H:28]([C@:29]5([CH3:32])[C@@H:16]([CH2:17][CH2:18]4)[C:15]([CH3:57])([CH3:58])[C@@H:14]([O:13][C:11](=[O:12])[CH2:10][C:2]([CH3:1])([CH3:59])[C:3]([OH:5])=[O:4])[CH2:31][CH2:30]5)[CH2:27][CH2:26]3)[CH2:47][CH2:46]2)=[N:49][CH:50]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117701492HCID 117701492, compound

Product 1

HCID 71611309HCID 71611309, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butyl 4-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((E)-3-((1-(5-chloropyrimidin-2-yl)cyclopropyl)amino)-3-oxoprop-1-en-1-yl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl) 2,2-dimethylsuccinate (300 mg, 0.360 mmol) in dichloromethane (5 mL) stirred at rt was added TFA (5 mL). The reaction mixture was stirred at rt for 2 h. It was evaporated in vacuo to give crude product which was purified by preparative HPLC to give the title compound (90 mg, 28%) as a light yellow solid. 1H NMR (300 MHz, DMSO-d6) δ=8.72 (s, 2H), 8.54 (br. s., 1H), 6.70 (d, J=15.8 Hz, 1H), 5.94 (d, J=15.8 Hz, 1H), 4.55-4.29 (m, 1H), 3.31-3.07 (m, 1H), 2.94-2.64 (m, 1H), 2.59-0.60 (m, 52H); LC/MS: m/z calculated 775.4. Found 776.3 (M+1)+.

Workup

  1. customIt was evaporated in vacuo
  2. customto give crude product which
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-b49c7aa11742445e82f568b537ac3f2b
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

Loading…