N-1-adamantyl-6-((triisopropylsilyloxy)methyl)-1H-benzo[d]imidazol-2-amine → N-(1-Adamanty-6-(hydroxymethyl)-1H-benzo[d]imidazol-2-yl)benzamide

HRID 518608Notes

Reaction equation

HRID 518608 reaction equation
[C:1]12([NH:11][C:12]3[NH:16][C:15]4[CH:17]=[C:18]([CH2:21][O:22][Si](C(C)C)(C(C)C)C(C)C)[CH:19]=[CH:20][C:14]=4[N:13]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.F[C:34]1[CH:63]=[CH:62][C:37]([C:38](/N=C2\NC3C=CC(CO)=CC=3N\2[C@@H]2CC[C@H](C(OC)=O)CC2)=[O:39])=[CH:36][CH:35]=1>>[C:1]12([N:11]3[C:15]4[CH:17]=[C:18]([CH2:21][OH:22])[CH:19]=[CH:20][C:14]=4[N:13]=[C:12]3[NH:16][C:38](=[O:39])[C:37]3[CH:62]=[CH:63][CH:34]=[CH:35][CH:36]=3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

3

Reactant 2

HCID 66728814N-1-adamantyl-6-((triisopropylsilyloxy)methyl)-1H-benzo[d]imidazol-2-amineHCID 178501185HCID 178501185, compound

Product 1

HCID 66728676N-(1-Adamanty-6-(hydroxymethyl)-1H-benzo[d]imidazol-2-yl)benzamide

Procedure

The title compound was prepared in 2 steps from N-1-adamantyl-6-((triisopropylsilyloxy)methyl)-1H-benzo[d]imidazol-2-amine using a method analogous to the preparation of cis-methyl 4-((E)-2-(4-fluorobenzoylimino)-6-(hydroxymethyl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylate. The yield was 200 mg (37.7%, 2 steps). MS m/z=402.2 [M+H]. Calc'd for C25H27N3O2: 401.2.

Sources & evidence

ORD record
ord-eac7ceff7c5c405587ebdb76d2a18839
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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