O-(cyclopropylmethyl)hydroxylamine hydrochloride → 6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-(3-oxo-3-pyrrolidin-1-yl-propyl)-3H-benzoimidazole-5-carboxylic acid cyclopropylmethoxy-amide

HRID 1767814Notes

Reaction equation

HRID 1767814 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([C:28](O)=[O:29])=[CH:11][C:12]3[N:16]([CH2:17][CH2:18][C:19](=[O:25])[N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)[CH:15]=[N:14][C:13]=3[C:26]=2[F:27])=[C:4]([Cl:31])[CH:3]=1.Cl.[CH:33]1([CH2:36][O:37][NH2:38])[CH2:35][CH2:34]1>>[CH:33]1([CH2:36][O:37][NH:38][C:28]([C:10]2[C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=3[Cl:31])=[C:26]([F:27])[C:13]3[N:14]=[CH:15][N:16]([CH2:17][CH2:18][C:19](=[O:25])[N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)[C:12]=3[CH:11]=2)=[O:29])[CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 11557279O-(cyclopropylmethyl)hydroxylamine hydrochlorideHCID 211142056-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-(3-oxo-3-pyrrolidin-1-yl-propyl)-3H-benzoimidazole-5-carboxylic acid

Product 1

HCID 113422276-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-(3-oxo-3-pyrrolidin-1-yl-propyl)-3H-benzoimidazole-5-carboxylic acid cyclopropylmethoxy-amide

Procedure

The title compound is prepared from 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-(3-oxo-3-pyrrolidin-1-yl-propyl)-3H-benzoimidazole-5-carboxylic acid and O-cyclopropylmethyl-hydroxylamine hydrochloride by the standard coupling procedure described in Step A: MS APCI (+) m/z 578, 580 (M+, Br pattern) detected; 1H NMR (400 MHz, DMSO-d6) δ 11.66 (s, 1H), 8.42 (s, 1H), 8.01 (s, 1H), 7.76 (s, 1H), 7.62 (s, 1H), 7.28 (d, 1H), 6.39 (890m, 1H), 4.52 (t, 2H), 3.66 (d, 2H), 3.33 (t, 2H), 3.28 (t, 2H), 2.89 (t, 2H), 1.83 (m, 2H), 1.76 (m, 2H), 1.06 (m, 1H), 0.49 (m, 2H), 0.22 (m, 2H); 19F NMR (376 MHz, DMSO-d6) −132.94 (s, 1F).

Sources & evidence

ORD record
ord-9718d974ba604e01910c130f0ccf2b43
Source dataset
uspto-grants-2007_06
Patent number
US07235537B2

Reaction notes

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