Ammonium Acetate → 6,6-Dimethyl-4-{3-methyl-2-(S)-[(tetrahydro-furan-3-carbonyl)-amino]-butyl}-morpholine-3-(S)-carboxylic acid (6-chloro-9H-b-carbolin-8-yl)-amide

HRID 552237Notes

Reaction equation

HRID 552237 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:16]([CH:18]3[CH2:23][O:22][C:21]([CH3:25])([CH3:24])[CH2:20][N:19]3[CH2:26][CH:27]([NH2:31])[CH:28]([CH3:30])[CH3:29])=[O:17])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[C:32]([O-:35])(=O)[CH3:33].[NH4+]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:16]([C@@H:18]3[CH2:23][O:22][C:21]([CH3:24])([CH3:25])[CH2:20][N:19]3[CH2:26][C@@H:27]([NH:31][C:16]([CH:18]3[CH2:33][CH2:32][O:35][CH2:23]3)=[O:17])[CH:28]([CH3:29])[CH3:30])=[O:17])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

3

Reactant 2

HCID 517165Ammonium AcetateHCID 671651234-(2-amino-3-methyl-butyl)-6,6-dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide

Product 1

HCID 113647286,6-Dimethyl-4-{3-methyl-2-(S)-[(tetrahydro-furan-3-carbonyl)-amino]-butyl}-morpholine-3-(S)-carboxylic acid (6-chloro-9H-b-carbolin-8-yl)-amide

Procedure

The desired compound was prepared following Method E from Intermediate 61 and the appropriate acid. 1H-NMR (300 MHz, methyl-d3 alcohol-d): δ 0.87 (m, 6H), 1.25 (d, 3H), 1.37 (d, 3H), 1.81 (m, 1H), 2.10-2.47 (m, 4H), 2.93 (m, 2H), 3.10 (m, 1H), 3.26 (m, 1H), 3.80 (m, 1H), 3.86-4.07 (m, 6H), 7.86 (d, 1H), 8.10 (m, 2H), 8.32 (d, 1H), 8.89 (s, 1H). Retention Time (LC, method: ammonium acetate standard): 1.73 min. MS (M+H+): 542.

Workup

  1. custom1.73 min

Sources & evidence

ORD record
ord-0e677ac0988548639d4549ac54b380b3
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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