2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → N-[6-Chloro-2-[(3S)-3-[[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]amino]-1-piperidinyl]-5-quinolinyl]-cyclohexaneacetamide

HRID 2217857Notes

Reaction equation

HRID 2217857 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:28])[C:14]=3[NH:18][C:19](=[O:27])[CH2:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[N:9]=2)[CH2:3]1.[Si:29]([O:36][CH2:37][CH:38]=O)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[Cl:28][C:13]1[C:14]([NH:18][C:19](=[O:27])[CH2:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([N:4]1[CH2:5][CH2:6][CH2:7][C@H:2]([NH:1][CH2:38][CH2:37][O:36][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH2:3]1)[CH:17]=[CH:16]2

Participants

4

Reactant 3

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11153851N-[2-[(3S)-3-Amino-1-piperidinyl]-6-chloro-5-quinolinyl]-cyclohexaneacetamide

Product 1

HCID 68808571N-[6-Chloro-2-[(3S)-3-[[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]amino]-1-piperidinyl]-5-quinolinyl]-cyclohexaneacetamide

Procedure

Prepared according to the method of example 50(a), using N-[2-[(3S)-3-amino-1-piperidinyl]-6-chloro-5-quinolinyl]-cyclohexaneacetamide (Example 60) (200 mg), (tert-butyldimethylsilyloxy)acetaldehyde (0.086 mL) and sodium triacetoxyborohydride (0.212 g) to afford the sub-title compound (0.2 g).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ea3892efef444bbf8e40b9735685e50c
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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