Ammonium Acetate → 6,6-Dimethyl-4-{-2-[(5-methyl-isoxazole-3-carbonyl)-amino]-propyl}-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide

HRID 552228Notes

Reaction equation

HRID 552228 reaction equation
[NH2:1][CH:2]([CH3:28])[CH2:3][N:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[O:7][CH2:6][CH:5]1[CH2:12][NH:13][C:14]1[CH:15]=[C:16]([Cl:27])[CH:17]=[C:18]2[C:26]=1[NH:25][C:24]1[CH:23]=[N:22][CH:21]=[CH:20][C:19]2=1.[CH3:29][C:30]1[O:34][N:33]=[C:32]([C:35](Cl)=[O:36])[CH:31]=1.C([O-])(=[O:40])C.[NH4+]>>[Cl:27][C:16]1[CH:17]=[C:18]2[C:26](=[C:14]([NH:13][C:12]([CH:5]3[CH2:6][O:7][C:8]([CH3:11])([CH3:10])[CH2:9][N:4]3[CH2:3][CH:2]([NH:1][C:35]([C:32]3[CH:31]=[C:30]([CH3:29])[O:34][N:33]=3)=[O:36])[CH3:28])=[O:40])[CH:15]=1)[NH:25][C:24]1[CH:23]=[N:22][CH:21]=[CH:20][C:19]2=1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 27368945-Methylisoxazole-3-carbonyl chlorideHCID 67165574[4-(2-Amino-propyl)-6,6-dimethyl-morpholin-3-ylmethyl]-(6-chloro-9H-beta-carbolin-8-yl)-amine

Product 1

HCID 671656296,6-Dimethyl-4-{-2-[(5-methyl-isoxazole-3-carbonyl)-amino]-propyl}-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amideYield 61%

Procedure

The desired compound was prepared using [4-(2-Amino-propyl)-6,6-dimethyl-morpholin-3-ylmethyl]-(6-chloro-9H-beta-carbolin-8-yl)-amine and 5-methylisoxazole carbonyl chloride following Method E in 61% yield. 1H-NMR (300 MHz, DMSO): δ 11.2 (1H, s), 9.98 (1H, s), 9.0 (1H, s), 8.7 (1H, d), 8.6 (1H, d), 8.2 (2H, m), 7.9 (1H, s). 6.47 (1H, s), 3.87 (2H, m), 3.17 (2H,m), 2.9 (1H, d), 2.7 (1H, m), 2.3 (4H), 2.1 (1H, d), 1.29 (3H, s), 1.15 (6H, m). Retention time (LC, method: ammonium acetate standard): 1.81 min. MS (M+H+): 526

Workup

  1. custom1.81 min

Sources & evidence

ORD record
ord-7b75391b1fb74a1b84b68d1a2be850bb
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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