Sodium triacetoxyborohydride → 4-(8-{4-[2-(4-Hydroxy-piperidin-1-yl)-thiazol-4-ylmethyl]-[1,4]diazepan-1-yl}-6-methyl-quinolin-7-yloxy)-butyric acid methyl ester

HRID 532850Notes

Reaction equation

HRID 532850 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[C:17]([N:18]2[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[C:16]2[C:11]([CH:12]=[CH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[CH3:25].[OH:27][CH:28]1[CH2:33][CH2:32][N:31]([C:34]2[S:35][CH:36]=[C:37]([CH:39]=O)[N:38]=2)[CH2:30][CH2:29]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[C:17]([N:18]2[CH2:24][CH2:23][CH2:22][N:21]([CH2:39][C:37]3[N:38]=[C:34]([N:31]4[CH2:30][CH2:29][CH:28]([OH:27])[CH2:33][CH2:32]4)[S:35][CH:36]=3)[CH2:20][CH2:19]2)=[C:16]2[C:11]([CH:12]=[CH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[CH3:25]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 593661612-(4-Hydroxy-piperidin-1-yl)-thiazole-4-carbaldehydeHCID 593662074-(8-[1,4]Diazepan-1-yl-6-methyl-quinolin-7-yloxy)-butyric acid methyl ester

Product 1

HCID 593661684-(8-{4-[2-(4-Hydroxy-piperidin-1-yl)-thiazol-4-ylmethyl]-[1,4]diazepan-1-yl}-6-methyl-quinolin-7-yloxy)-butyric acid methyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

The product from step 2 (3.63 mmol) was dissolved in 1,2-dichloroethane (7.26 mL), and 2-(4-Hydroxy-piperidin-1-yl)-thiazole-4-carbaldehyde (771 mg, 3.63 mmol) was then added. This solution was stirred for 1 h, then NaBH(OAc)3 (1.54 g, 7.26 mmol) was added. The solution was stirred for 2 h, then diluted with CH2Cl2. The solution was washed with sat. aq. NaHCO3, then brine. The organic was dried over MgSO4, filtered, and concentrated to give the crude product. This was carried on without further purification.

Workup

  1. stirringThe solution was stirred for 2 h
  2. washThe solution was washed with sat. aq. NaHCO3
  3. dry with materialThe organic was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b760c282397468abe0f6ffd8c5768e7
Source dataset
uspto-grants-2014_10
Patent number
US08853202B2

Reaction notes

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