Bicarbonate Ion → HCID 59471695, compound

HRID 78624Notes

Reaction equation

HRID 78624 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9]1[C:10]([C:26]2[O:30][C:29]([C:31]3[CH:32]=[C:33]([CH2:37][NH:38]C(=O)OC(C)(C)C)[CH:34]=[CH:35][CH:36]=3)=[N:28][N:27]=2)=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:25])[N:22]([CH3:24])[CH3:23])=[CH:17][CH:16]=2)=[CH:13][N:14]=1.C(=O)(O)[O-]>ClCCl.CO>[NH2:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([N:22]([CH3:24])[CH3:23])=[O:25])=[CH:19][CH:20]=2)=[N:11][C:10]=1[C:26]1[O:30][C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][NH2:38])[CH:32]=2)=[N:28][N:27]=1

Participants

6

Reactant 3

HCID 769Bicarbonate IonHCID 6422Trifluoroacetic acidHCID 59471932HCID 59471932, compound

Product 1

HCID 59471695HCID 59471695, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

TFA (131.1 mg, 88.58 μL, 1.150 mmol) was added to a solution of tert-butyl N-[[3-[5-[3-amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]carbamate (60 mg, 0.1150 mmol) in dichloromethane (2 mL) and the resulting solution stirred at room temperature overnight. The reaction mixture was passed through a bicarbonate cartridge, which was flushed further with methanol (5 mL). The filtrate was concentrated in vacuo to leave a yellow/orange solid. The solid was taken up in a mixture of methanol and dichloromethane and passed through an SCX cartridge. The cartridge was washed initially with methanol and then the product eluted with 2M ammonia in methanol solution over 4 fractions. A yellow solid crystallised out of the filtrate which was isolated by filtration to give the product (44 mg, 90% yield) 1H NMR (400 MHz, DMSO) d 2.98 (m, 6H), 3.87 (s, 2H), 7.55 (m, 2H), 7.59-7.66 (m, 2H), 7.81 (br s, 2H), 8.00 (m, 1H), 8.17 (m, 3H) and 8.99 (s, 1H) ppm; MS (ES+) 416.26

Workup

  1. customwas flushed further with methanol (5 mL)
  2. concentrationThe filtrate was concentrated in vacuo
  3. customto leave a yellow/orange solid
  4. washThe cartridge was washed initially with methanol
  5. washthe product eluted with 2M ammonia in methanol solution over 4 fractions
  6. customA yellow solid crystallised out of the filtrate which
  7. customwas isolated by filtration

Sources & evidence

ORD record
ord-f9c1f81aa5aa467d91329ae12d16c0b9
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

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