Dichloromethane → HCID 69588611, compound

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([CH2:16][C:17]2[N:18]=[C:19]([CH2:22][CH2:23][CH2:24][CH:25]=O)[S:20][CH:21]=2)[CH2:10][C:11]([O:13]CC)=[O:12])=[CH:5][CH:4]=1.[N:27]1([C:33]2[CH:38]=[CH:37][N:36]=[C:35]([NH2:39])[CH:34]=2)[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(Cl)[Cl:55]>>[ClH:55].[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([CH2:16][C:17]2[N:18]=[C:19]([CH2:22][CH2:23][CH2:24][CH2:25][NH:39][C:35]3[CH:34]=[C:33]([N:27]4[CH2:28][CH2:29][O:30][CH2:31][CH2:32]4)[CH:38]=[CH:37][N:36]=3)[S:20][CH:21]=2)[CH2:10][C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 5049666Sodium triacetoxyborohydride

HCID 219345374-(Morpholin-4-yl)pyridin-2-amine

HCID 21934557HCID 21934557, compound

Product 1

HCID 69588611HCID 69588611, compound

Procedure

Dissolve ethyl 3-(6-methoxypyridin-3-yl)-4-[2-(4-oxobutyl)-1,3-thiazol-4-yl]butanoate (374mg, 1.0 mmol) and 4-morpholin-4-ylpyridin-2-amine (150 mg, 0.836 mmol) prepared according to Scheme 6, Example 1, in CH2Cl2. Add NaBH(OAc)3 (251 mg, 1.12 mmol) and stir at room temperature for 18 hours. The reaction was concentrated in vacuo and purified via reverse phase HPLC using a gradient of 10–60% CH3CN/H2O/0.5% HCl over 30 minutes to obtain the crude desired product.