(4-Chlorophenyl)acetic acid → HCID 178455450, compound

HRID 82244

Reaction equation

HRID 82244 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:18]3[CH:17]=[N:16][CH:15]=[N:14][C:13]=3[N:12]([C:19]3([C:23]([CH3:31])([CH3:30])[O:24][SiH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][O:21][CH2:20]3)[CH:11]=2)=[O:9])[CH:5]=[N:6][CH:7]=1.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][C:40](O)=[O:41])=[CH:35][CH:34]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>N1C=CC=CC=1.ClCCl.C(=O)(O)[O-].[Na+]>[C:26]([SiH2:25][O:24][C:23]([CH3:31])([CH3:30])[C:19]1([N:12]2[C:13]3[N:14]=[CH:15][N:16]=[CH:17][C:18]=3[C:10]([C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:40](=[O:41])[CH2:39][C:36]4[CH:37]=[CH:38][C:33]([Cl:32])=[CH:34][CH:35]=4)[CH:7]=[N:6][CH:5]=3)=[O:9])=[CH:11]2)[CH2:20][O:21][CH2:22]1)([CH3:29])([CH3:28])[CH3:27]

Participants

7

Reactant 3

HCID 15880(4-Chlorophenyl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178455448HCID 178455448, compound

Product 1

HCID 178455450HCID 178455450, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

(5-Amino-pyridin-3-yl)-{7-[3-(tert-butyl-dimethyl-silanyloxymethyl)-oxetan-3-yl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-methanone (Preparation 216, 30 mg, 0.068 mmol) was dissolved in dry pyridine (2 mL) under nitrogen and to this was added (4-chloro-phenyl)-acetic acid (17 mg, 0.102 mmol), followed by HATU (39 mg, 0.102 mmol). The reaction was heated to 50° C. and stirred overnight. The reaction was cooled to room temperature, diluted with dichloromethane and saturated aqueous sodium bicarbonate was added. The phases were separated and the aqueous layer was extracted with dichloromethane (3×5 mL). The combined organics were concentrated to dryness to afford N-(5-{7-[3-(tert-butyl-dimethyl-silanyloxymethyl)-oxetan-3-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl}-pyridin-3-yl)-2-(4-chloro-phenyl)-acetamide as a pale yellow solid 35 mg, 87% yield.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. additionwas added
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (3×5 mL)
  5. concentrationThe combined organics were concentrated to dryness

Sources & evidence

ORD record
ord-6ab43cf5f81644b7aa47ba6116426b01
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Linked notes

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