Butyrophenone → HCID 178438245, compound

HRID 897919Notes

Reaction equation

HRID 897919 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:26]3[CH2:31][CH2:30][C@@H:29]([N:32]4[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]4)[CH2:28][CH2:27]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]4[S:19][C:20]5[CH2:25][CH2:24][CH2:23][C:21]=5[N:22]=4)=[CH:13][CH:12]=3)[C:3]=12.[C:39]([C:44]1C=CC=C[CH:45]=1)(=O)[CH2:40][CH2:41]C>>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:26]3[CH2:31][CH2:30][C@@H:29]([N:32]4[CH2:33][CH2:34][N:35]([CH3:38])[CH2:36][CH2:37]4)[CH2:28][CH2:27]3)[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([NH:17][C:18]4[S:19][C:20]([CH2:25][CH3:24])=[C:21]([C:23]5[CH:45]=[CH:44][CH:39]=[CH:40][CH:41]=5)[N:22]=4)=[CH:15][CH:16]=3)[C:3]=12

Participants

3

Reactant 2

HCID 10315ButyrophenoneHCID 178480980HCID 178480980, compound

Product 1

HCID 178438245HCID 178438245, compound

Procedure

The procedure for the preparation of cis-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5,6-dihydro-4H-cyclopenta[d][1,3]thiazol-2-amine was used to convert butyrophenone (436 μL, 3.00 mmol) to the title compound. Purification of the product by preparative HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 20 min at 21 mL/min using an 8μ Hypersil HS C18, 250×21 mm column, Rt 8.9-11.1 min) afforded cis-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5-ethyl-4-phenyl-1,3-thiazol-2-amine as a white powder (0.022 g, 0.037 mmol); RP-HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 10 min at 1 mL/min using a 5μ Hypersil HS C18, 250×4.6 mm column) Rt 9.27 min;

Sources & evidence

ORD record
ord-e176e0b8e7a14db8beacb8e8365ddd00
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

Loading…