Sodium triacetoxyborohydride → HCID 68751156, compound

HRID 1851266Notes

Reaction equation

[CH3:1][C:2]1[N:24]=[C:5]2[N:6]=[C:7]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1.Cl.[NH:26]1[CH2:31][CH2:30][CH:29]([C:32]2[NH:40][C:35]3[CH:36]=[N:37][CH:38]=[CH:39][C:34]=3[N:33]=2)[CH2:28][CH2:27]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[N:33]1[C:34]2[CH:39]=[CH:38][N:37]=[CH:36][C:35]=2[NH:40][C:32]=1[CH:29]1[CH2:30][CH2:31][N:26]([CH2:20][C:19]2[CH:22]=[CH:23][C:16]([C:7]3[C:8]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)=[CH:9][N:4]4[N:3]=[C:2]([CH3:1])[N:24]=[C:5]4[N:6]=3)=[CH:17][CH:18]=2)[CH2:27][CH2:28]1

Participants

Reactant 3

HCID 5049666Sodium triacetoxyborohydride

HCID 68752438HCID 68752438, compound

HCID 866306814-(2-Methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

Product 1

HCID 68751156HCID 68751156, compoundYield 33.7%

Procedure

200 mg (0.64 mmol) 4-(2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde and 181 mg (0.76 mmol) 2-piperidine-4-yl-3H-imidazo[4,5-c]pyridine hydrochloride salt were treated as described in example 2.0. Additional NaBH(OAc)3 has been added after one, two, three, four and a half, five and a half, and seven and a half hours (two equivalents each). The solvents were evaporated and the usual workup and purification yields 108 mg of the desired compound.

Workup

customa half, and seven and a half hours (two equivalents each)
customThe solvents were evaporated
customthe usual workup and purification

Sources & evidence

ORD record: ord-40b5d8c6e597448cbbc9712b5d9305bb
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957064B2

Reaction notes

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