Formic Acid → HCID 11752837, compound

HRID 2099770Notes

Reaction equation

HRID 2099770 reaction equation
[O:1]=[C:2]1[N:11]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH:21]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([O:39]C(C)(C)C)[N:34]=3)[CH2:22][C:23]3[CH:24]=[C:25]4[C:29](=[C:30]([CH3:32])[CH:31]=3)[NH:28][N:27]=[CH:26]4)=[O:19])[CH2:14][CH2:13]2)[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C(O)=O>O>[O:1]=[C:2]1[N:11]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH:21]([C:33]3[NH:34][C:35](=[O:39])[CH:36]=[CH:37][CH:38]=3)[CH2:22][C:23]3[CH:24]=[C:25]4[C:29](=[C:30]([CH3:32])[CH:31]=3)[NH:28][N:27]=[CH:26]4)=[O:19])[CH2:14][CH2:13]2)[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 11376694HCID 11376694, compound

Product 1

HCID 11752837HCID 11752837, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Solid (±)-1-(6-tert-butoxypyridin-2-yl)-2-(7-methyl-1H-indazol-5-yl)ethyl 4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidine-1-carboxylate (previous example) (20.6 mg) was treated with 1 mL formic acid (90%). After 2 h, the mixture was diluted with water and extracted three times with ethyl acetate. The combined organic layers were washed with water, saturated sodium bicarbonate solution, dried and concentrated. Further drying under high vacuum afforded the product (11.8 mg, 63.4%) as an off-white powder. MS (ESI) [M+H]+=527. HPLC tR=1.68 min.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed with water, saturated sodium bicarbonate solution
  3. customdried
  4. concentrationconcentrated
  5. customFurther drying under high vacuum

Sources & evidence

ORD record
ord-64965a9b0016470db450a5b79962daef
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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