Water → HCID 53241939, compound

HRID 1505420Notes

Reaction equation

HRID 1505420 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]([O:10][C:11]2[N:16]=[CH:15][C:14]([NH:17][C:18](=[O:22])[C@@H:19]([CH3:21])[NH2:20])=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:3].Cl[C:24](Cl)([O:26]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.O>ClCCl>[CH3:21][C@H:19]1[NH:20][C:24](=[O:26])[N:17]([C:14]2[CH:13]=[N:12][C:11]([O:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]=3)=[N:16][CH:15]=2)[C:18]1=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94429TriphosgeneHCID 67236472HCID 67236472, compound2×

Product 1

HCID 53241939HCID 53241939, compoundYield 230.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N1-(2-{[3-(1-methylethyl)phenyl]oxy}-5-pyrimidinyl)-D-alaninamide (Intermediate 87, 100 mg) in dichloromethane (30 mL) were added triphosgene (40 mg, 0.133 mmol) and triethylamine (51 mg, 0.5 mmol). The resulting mixture was stirred at 0° C. for 30 minutes and water (30 mL) was added. It was extracted with dichloromethane (3 times 30 mL) and the combined organic layer was dried over sodium sulphate and evaporated to afford the title compound (100 mg).

Workup

  1. extractionIt was extracted with dichloromethane (3 times 30 mL)
  2. dry with materialthe combined organic layer was dried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-5ac2a32647fd41dc9c9633e63df9ca18
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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