Dichloromethane → HCID 86595789, compound

HRID 1241449Notes

Reaction equation

HRID 1241449 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@@H:10]([CH2:17][C:18]3[N:19]=[C:20]([CH2:23][CH2:24][CH2:25][CH:26]=O)[S:21][CH:22]=3)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[N:28]1([C:34]2[CH:39]=[CH:38][N:37]=[C:36]([NH2:40])[CH:35]=2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C1COCC1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(Cl)[Cl:61]>>[ClH:61].[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@@H:10]([CH2:17][C:18]3[N:19]=[C:20]([CH2:23][CH2:24][CH2:25][CH2:26][NH:40][C:36]4[CH:35]=[C:34]([N:28]5[CH2:33][CH2:32][O:31][CH2:30][CH2:29]5)[CH:39]=[CH:38][N:37]=4)[S:21][CH:22]=3)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydride2×HCID 219345374-(Morpholin-4-yl)pyridin-2-amineHCID 86595788HCID 86595788, compound

Product 1

HCID 86595789HCID 86595789, compound

Procedure

Dissolve (3S)-Ethyl 3-(1,3-benzodioxol-5-yl)-4-[2-(4-oxobutyl)-1,3-thiazol-4-yl]butanoate (230 mg, 0.6 mmol) and 4-morpholin-4-ylpyridin-2-amine (88 mg, 0.5 mmol) prepared according to Scheme 6, Example 1, in CH2Cl2. Add 3 mL THF and add NaBH(OAc)3. Stir at room temperature for 18 hours. Add 1.0 eq NaBH(OAc)3 and stir 24 hrs. 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. stirringstir 24 hrs
  3. concentrationThe reaction was concentrated in vacuo
  4. custompurified via reverse phase HPLC
  5. customover 30 minutes

Sources & evidence

ORD record
ord-03a1df963e514719a66a7cb809f25ad0
Source dataset
uspto-grants-2006_10
Patent number
US07115596B2

Reaction notes

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