Sodium triacetoxyborohydride → HCID 11192748, compound

HRID 2099759Notes

Reaction equation

HRID 2099759 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][CH:12]([C:33]2[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][N:34]=2)[CH2:13][C:14](=[O:32])[N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[CH2:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:23][C:22]3=[O:31])[CH2:17][CH2:16]2)[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[BH-](O[C:51]([CH3:53])=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.N1CCCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][CH:12]([C:33]2[CH:40]=[CH:39][C:36]([CH2:37][N:8]3[CH2:53][CH2:51][CH2:5][CH2:6][CH2:7]3)=[CH:35][N:34]=2)[CH2:13][C:14]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[CH2:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:23][C:22]3=[O:31])[CH2:17][CH2:16]2)=[O:32])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2

Participants

5

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 11341642HCID 11341642, compound

Product 1

HCID 11192748HCID 11192748, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

A solution of (±)-6-(1-(7-methyl-1H-indazol-5-yl)-4-oxo-4-(4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidin-1-yl)butan-2-yl)nicotinaldehyde (previous example, 8 mg, 0.015 mmol, 1.0 equiv.) in dichloroethane (1 mL) was treated with by 2 drops of piperidine. Excess Na(OAc)3BH was added and the reaction mixture was stirred at room temperature overnight. The mixture was directly purified by flash column chromatography (10% of 2M ammonia in methanol in methylene chloride) afforded the desired product (10.1 mg, 72% for two steps).

Workup

  1. customThe mixture was directly purified by flash column chromatography (10% of 2M ammonia in methanol in methylene chloride)

Sources & evidence

ORD record
ord-6954e45f22dc4ac7bc0329e3490a509c
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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