1,2-Dichloroethane → HCID 24784974, compound

HRID 2243647Notes

Reaction equation

HRID 2243647 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([N:29]3[CH2:34][CH2:33][CH:32]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:31][CH2:30]3)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:22](O)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:43].C(Cl)CCl.C1[CH:49]=[CH:50][C:51]2N(O)N=[N:54][C:52]=2C=1.C1(CN)CC1>C(Cl)Cl>[CH:51]1([CH2:52][NH:54][C:22]([C:21]2[CH:25]=[CH:26][C:27]([CH3:28])=[C:19]([C:18]3[C:13]4[CH2:12][NH:11][C:10](=[O:43])[N:9]([C:3]5[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=5[F:1])[C:14]=4[N:15]=[C:16]([N:29]4[CH2:30][CH2:31][CH:32]([NH:35][C:36](=[O:37])[O:38][C:39]([CH3:41])([CH3:42])[CH3:40])[CH2:33][CH2:34]4)[N:17]=3)[CH:20]=2)=[O:23])[CH2:49][CH2:50]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 75646CyclopropanemethanamineHCID 757711-HydroxybenzotriazoleHCID 59207995HCID 59207995, compound

Product 1

HCID 24784974HCID 24784974, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{8-(2,6-Difluorophenyl)-2-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl}-4-methylbenzoic acid (250 mg) in methylenechloride (100 mL) were added EDC (100 mg), HOBt (70 mg) and cyclopropylmethylamine (110 uL). The reaction was stirred at r.t. overnight and evaporated in vacuo. Flash chromatography then provided the title compound as a white solid. LC-MS m/z 648 (M+H)+, 2.33 min (ret. time).

Workup

  1. customevaporated in vacuo

Sources & evidence

ORD record
ord-1d42ae8223f0444f862f0dbb046ab9e3
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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