2-Methoxyethanol → HCID 66829910, compound
Reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:13][CH2:12][CH2:11][C@H:10]2[C:14]([NH2:16])=[O:15])[C:5]([Cl:17])=[CH:4][N:3]=1.[CH2:18]([N:20]1[CH2:26][CH2:25][C:24]2[CH:27]=[C:28]([NH2:31])[CH:29]=[CH:30][C:23]=2[CH2:22][CH2:21]1)[CH3:19].COCCO.Cl.O1CCOCC1>>[Cl:17][C:5]1[C:6]([NH:8][C@H:9]2[CH2:13][CH2:12][CH2:11][C@H:10]2[C:14]([NH2:16])=[O:15])=[N:7][C:2]([NH:31][C:28]2[CH:29]=[CH:30][C:23]3[CH2:22][CH2:21][N:20]([CH2:18][CH3:19])[CH2:26][CH2:25][C:24]=3[CH:27]=2)=[N:3][CH:4]=1Participants
Procedure
Into a microwave vial was added cis-2-(2,5-dichloro-pyrimidin-4-ylamino)-cyclopentane-carboxylic acid amide (80 mg, 0.0003 mol) and 3-ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine (61 mg, 0.00032 mol) in 2-methoxyethanol (4 mL, 0.06 mol). To this reaction mixture was added 4N HCl-dioxane (0.04 g, 0.0003 mol) and the contents subjected to microwaves at 120° C. for 10 min. HPLC indicated no starting material remaining. A solid had precipitated out of the reaction mixture and was collected by filtration. The white solid was dried in vacuum at 50° C. overnight to give cis-2-[5-Chloro-2-(3-ethyl-2,3,4,5-tetrahydro-1H-benzo[d]-azepin-7-ylamino)-pyrimidin-4-ylamino]-cyclopentanecarboxylic acid amide (30 mg, 20%). MP: 237-242° C.; 1HNMR (400 MHz, DMSO-d6) δ 10.28 (s, 1H), 9.73 (s, 1H), 8.06 (s, 1H), 7.60 (s, 1H), 7.58 (d, 1H, J=), 7.46 (m, 1H), 7.16 (m, 2H), 4.43 (m, 1H), 3.62 (m, 5H), 3.18 (m, 2H), 2.87-2.98 (m, 4H), 1.59-1.75 (m, 5H), 1.59 (m, 1H), 1.27 (t, 3H, J=7.3 Hz); MS (m/e) 429 (M+1).
Workup
- customA solid had precipitated out of the reaction mixture
- filtrationwas collected by filtration
- customThe white solid was dried in vacuum at 50° C. overnight
Sources & evidence
- ORD record
- ord-c3dfbf98afd44d44aa05ff0919745d0e
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552186B2
Reaction notes
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