(2R)-1-aminopropan-2-ol → HCID 69480479, compound

HRID 2364560Notes

Reaction equation

HRID 2364560 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:36])=[C:14]([C:31](OCC)=[O:32])[C:15](=[O:30])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:29])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:37][CH2:38][C@H:39]([OH:41])[CH3:40]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:36])=[C:14]([C:31]([NH:37][CH2:38][C@H:39]([OH:41])[CH3:40])=[O:32])[C:15](=[O:30])[N:16]3[CH2:19][CH2:20][CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]3=[O:29])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 439938(2R)-1-aminopropan-2-olHCID 69481817HCID 69481817, compound

Product 1

HCID 69480479HCID 69480479, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[3-(2-oxohexahydro-1H-azepin-1-yl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and (2R)-1-amino-2-propanol using methods similar to Example 563 to provide an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.06-1.12 (m, 4 H), 1.54 (d, J=5.05 Hz, 4 H), 1.60-1.75 (m, 4 H), 2.36-2.45 (m, 2 H), 3.15-3.25 (m, 1 H), 3.32-3.47 (m, 4 H), 3.82 (ddd, J=10.84, 6.63, 4.42 Hz, 1 H), 4.15-4.24 (m, 4 H), 4.96 (d, J=4.84 Hz, 1 H) 7.10-7.18 (m, 2 H), 7.38-7.44 (m, 2 H), 8.00 (d, J=1.26 Hz, 1 H), 8.56 (d, J=1.47 Hz, 1 H), 10.44 (t, J=5.58 Hz, 1 H), 17.21 (s, 1 H); ES+ MS: 525 (M+H+).

Workup

  1. customto provide an off-white solid

Sources & evidence

ORD record
ord-e9db3b3bdb4b4ebeb122397e6023c565
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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