2-Chloro-4-methylpyrimidine → 2-Propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-4-fluorophenyl}carbamate

HRID 1671138Notes

Reaction equation

HRID 1671138 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:23])[O:19][CH2:20][CH:21]=[CH2:22])[CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=[CH:4][N:3]=1.[F:24]C1C=CC(NC(OCC=C)=O)=CC=1C(OC)=O.ClC1N=C(C)C=CN=1>>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:23])[O:19][CH2:20][CH:21]=[CH2:22])[CH:14]=[CH:15][C:16]=2[F:24])=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 116296072-Chloro-4-methylpyrimidineHCID 579899812-Propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]phenyl}carbamateHCID 57990057Methyl 2-fluoro-5-{[(2-propen-1-yloxy)carbonyl]amino}benzoate

Product 1

HCID 579897622-Propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-4-fluorophenyl}carbamateYield 69.9%

Procedure

Using multiple iterations of a procedure analogous to the procedure described in Intermediate 11 using methyl 2-fluoro-5-{[(2-propen-1-yloxy)carbonyl]amino}benzoate (104 g, 411 mmol) and 2-chloro-4-methylpyrimidine (59 g, 493 mmol), the title compound of Step B was obtained (100 g, 69.9% yield). 1H NMR (400 MHz, CDCl3) δ ppm 13.67-13.75 (br, 1H), 8.50-8.53 (m, 0.3H), 8.31-8.38 (m, 1H), 7.50-7.82 (m, 2.6H), 6.56-7.20 (m, 3.5H), 6.20-6.25 (m, 1H), 5.82-6.01 (1.3H), 5.20-5.40 (m, 2.6H), 4.50-4.61 (m, 2.6H), 4.31-4.41 (m, 0.9H).

Sources & evidence

ORD record
ord-f13ccc41e60c429bae166e4318df52d6
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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