4-Carbazol-9-ylmethyl-N-hydroxybenzamide → 6-[6-(4-Dimethylamino-phenyl)-1,2,3,4-tetrahydro-carbazol-9-yl]-hexanoic acid hydroxyamide

HRID 403649Notes

Reaction equation

HRID 403649 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[C:14]([C:23]1[CH:28]=[CH:27][C:26]([N:29]([CH3:31])[CH3:30])=[CH:25][CH:24]=1)[CH:15]=2)C.C1C2N(CC3C=CC(C([NH:53][OH:54])=O)=CC=3)C3C(=CC=CC=3)C=2C=CC=1>>[OH:54][NH:53][C:4](=[O:3])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[C:14]([C:23]1[CH:28]=[CH:27][C:26]([N:29]([CH3:31])[CH3:30])=[CH:25][CH:24]=1)[CH:15]=2

Participants

3

Reactant 2

HCID 469188244-Carbazol-9-ylmethyl-N-hydroxybenzamideHCID 668904806-[6-(4-Dimethylamino-phenyl)-1,2,3,4-tetrahydro-carbazol-9-yl]-hexanoic acid ethyl ester2×

Product 1

HCID 866717206-[6-(4-Dimethylamino-phenyl)-1,2,3,4-tetrahydro-carbazol-9-yl]-hexanoic acid hydroxyamide

Procedure

Compound 33 was prepared from 6-(6-bromo-1,2,3,4-tetrahydro-carbazol-9-yl)-hexanoic acid ethyl ester (compound 32) using the procedure described above for compound 29 as a white solid (85%). 1H NMR (400 MHz, MeOD): δ 7.86 (d, 2H), 7.65 (m, 3H), 7.33 (s, 2H), 4.09 (t, 2H), 2.76 (m, 4H), 2.16 (s, 1H), 2.08 (t, 2H), 1.98 (m, 2H), 1.90 (m, 2H), 1.77 (m, 2H), 1.66 (m, 2H), 1.38 (m, 2H).

Sources & evidence

ORD record
ord-e473a4c26cbb4b69b55a38af01f5004c
Source dataset
uspto-grants-2014_06
Patent number
US08748451B2

Reaction notes

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