2-(Propylamino)ethanol → (1E,4E)-2-amino-N-(2-hydroxyethyl)-N-propyl-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxamide

HRID 593431Notes

Reaction equation

HRID 593431 reaction equation
C(OC([NH:8][C:9]1[CH2:10][C:11]([C:33](O)=[O:34])=[CH:12][C:13]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[O:27])=[CH:22][CH:21]=3)=[CH:16][C:14]=2[N:15]=1)=O)(C)(C)C.[Si]([O:43][CH2:44][CH2:45][NH:46][CH2:47][CH2:48][CH3:49])(C(C)(C)C)(C)C.C(NCCO)CC>>[NH2:8][C:9]1[CH2:10][C:11]([C:33]([N:46]([CH2:45][CH2:44][OH:43])[CH2:47][CH2:48][CH3:49])=[O:34])=[CH:12][C:13]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[CH:22][C:23]([C:26]([N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[O:27])=[CH:24][CH:25]=3)=[CH:16][C:14]=2[N:15]=1

Participants

4

Reactant 3

HCID 853822-(Propylamino)ethanolHCID 66960164(1E,4E)-2-(tert-butoxycarbonylamino)-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxylic acidHCID 86653470N-(2-((tert-butyldimethylsilyl)oxy)ethyl)propan-1-amine

Product 1

HCID 51033410(1E,4E)-2-amino-N-(2-hydroxyethyl)-N-propyl-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxamide

Procedure

The title compound was prepared by the procedures as described in Example 104 using (1E,4E)-2-(tert-butoxycarbonylamino)-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxylic acid and N-(2-(tert-butyldimethylsilyloxy)ethyl)propan-1-amine that was prepared by the procedure as described in Example 104 (Step A) using 2-(propylamino)ethanol. MS APCI (+) m/z 461 (M+1) detected; 1H-NMR (400 MHz, CDCl3) δ 7.68 (d, 2H), 7.60 (d, 2H), 7.49 (s, 1H), 7.29-7.35 (m, 2H), 6.88 (s, 1H), 3.84 (s, 2H), 3.67 (t, 4H), 3.50 (t, 4H), 2.84 (s, 2H), 1.88-2.00 (m, 4H), 1.66-1.72 (m, 2H), 0.93 (t, 3H).

Workup

  1. customwas prepared by the procedure

Sources & evidence

ORD record
ord-3e2c2434a87b4f6fa0d762a364180cdb
Source dataset
uspto-grants-2016_01
Patent number
US09242964B2

Reaction notes

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