(7-Nitro-1H-benzimidazol-1-yl)acetic acid → N-[(1S)-1-(4-hydroxyphenyl)ethyl]-2-(7-nitro-1H-benzimidazol-1-yl)acetamide

HRID 1919819Notes

Reaction equation

HRID 1919819 reaction equation
[N+:1]([C:4]1[C:9]2[N:10]([CH2:13][C:14]([OH:16])=O)[CH:11]=[N:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:17][C@H:18]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[CH3:19]>>[OH:26][C:23]1[CH:24]=[CH:25][C:20]([C@@H:18]([NH:17][C:14](=[O:16])[CH2:13][N:10]2[C:9]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[CH:7][C:8]=3[N:12]=[CH:11]2)[CH3:19])=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 11379027(7-Nitro-1H-benzimidazol-1-yl)acetic acidHCID 41097924(S)-4-(1-Aminoethyl)phenol

Product 1

HCID 67500286N-[(1S)-1-(4-hydroxyphenyl)ethyl]-2-(7-nitro-1H-benzimidazol-1-yl)acetamide

Procedure

The title compound was synthesised according to the general method of synthesis of target compounds (see below) from (7-nitro-1H-benzimidazol-1-yl)acetic acid and 4-[(1S)-1-aminoethyl]phenol. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.26 (s, 1 H) 8.55 (d, J=8.03 Hz, 1 H) 8.40 (s, 1 H) 8.10 (d, J=8.03 Hz, 1 H) 7.98 (d, J=7.53 Hz, 1 H) 7.39 (t, J=8.03 Hz, 1 H) 7.05-7.15 (m, 2 H) 6.64-6.75 (m, 2 H) 5.19 (s, 2 H) 4.71-4.83 (m, 1 H) 1.32 (d, J=6.78 Hz, 3 H). MS (ESI) m/z: 341 [M+H]

Sources & evidence

ORD record
ord-192c73525af94014a5c4e0f3db820010
Source dataset
uspto-grants-2012_05
Patent number
US08168668B2

Reaction notes

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