Dichloromethane → HCID 69588611, compound

HRID 1241451Notes

Reaction equation

HRID 1241451 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

5

Reactant 4

HCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 219345374-(Morpholin-4-yl)pyridin-2-amineHCID 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.

Workup

  1. customprepared
  2. concentrationThe reaction was concentrated in vacuo
  3. custompurified via reverse phase HPLC
  4. customover 30 minutes

Sources & evidence

ORD record
ord-b349c9cb361a4abbbbb8e173fa6df7ce
Source dataset
uspto-grants-2006_10
Patent number
US07115596B2

Reaction notes

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