Water → HCID 53241939, compound

HRID 1023615Notes

Reaction equation

HRID 1023615 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 N-(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). 1HNMR (400 MHz, CDCl3): δ ppm 8.62 (2H, s), 7.26-7.30 (1H, t), 7.08-7.05 (2H, m), 6.99-6.92 (2H, m), 4.22-4.20 (1H, d), 2.88-2.84 (1H, m), 1.47-1.45 (3H, d), 1.19-1.18 (6H, d); MS—2 (ESI): 326 [M+H]+.

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-4e20c4ba31c446db84305cbf38ce47f3
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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