4,4-Difluoropiperidine → HCID 86656969, compound

HRID 411047Notes

Reaction equation

HRID 411047 reaction equation
O=[CH:2][CH2:3][NH:4][C:5]([C:7]1[CH:27]=[CH:26][C:10]2[N:11]([CH3:25])[C:12]([NH:14][C:15]3[S:16][C:17]4[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:18]=4[N:19]=3)=[N:13][C:9]=2[CH:8]=1)=[O:6].[F:28][C:29]1([F:35])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[F:28][C:29]1([F:35])[CH2:34][CH2:33][N:32]([CH2:2][CH2:3][NH:4][C:5]([C:7]2[CH:27]=[CH:26][C:10]3[N:11]([CH3:25])[C:12]([NH:14][C:15]4[S:16][C:17]5[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:18]=5[N:19]=4)=[N:13][C:9]=3[CH:8]=2)=[O:6])[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 27583524,4-DifluoropiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86656968HCID 86656968, compound

Product 1

HCID 86656969HCID 86656969, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(6-Chloro-benzothiazol-2-ylamino)-1-methyl-1H-benzoimidazole-5-carboxylic acid [2 (4,4-difluoro-piperidin-1-yl)-ethyl]-amide (45 mg) was prepared by following General Procedure P starting from 2-(6-chloro-benzothiazol-2-ylamino)-1-methyl-1H-benzoimidazole-5-carboxylic acid (2-oxo-ethyl)-amide (80 mg), 4,4-difluoro-piperidine (36 mg), and Na(OAc)3BH (65 mg) in DCM (2 mL). LC/MS: m/z 504.5. 1H NMR (DMSO-d6, 400 MHz): δ 8.97-8.88 (m, 1H), 8.14-8.12 (m, 1H), 7.97-7.96 (m, 1H), 7.88-7.80 (m, 1H), 7.56-7.52 (m, 2H), 7.43-7.40 (m, 1H), 4.08-4.05 (m, 1H), 3.74-3.69 (m, 7H), 3.57-3.47 (m, 1H), 3.46-3.17 (m, 3H), 2.46-2.43 (m, 3H), —NH proton signal was not observed.

Sources & evidence

ORD record
ord-ed35ba5bf79543d39c78b7c4f035b749
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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