HCID 178476643, compound → HCID 178480943, compound

HRID 51574Notes

Reaction equation

C(O)(=O)C.C[O:6][C:7]1[CH:8]=[C:9]([C:20]2[C:28]3[C:27]([NH2:29])=[N:26][CH:25]=[N:24][C:23]=3[N:22]([C@H:30]3[CH2:35][CH2:34][C@H:33]([N:36]4[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]4)[CH2:32][CH2:31]3)[CH:21]=2)[CH:10]=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>Br>[NH2:29][C:27]1[C:28]2[C:20]([C:9]3[CH:10]=[CH:11][C:12]([O:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)=[C:7]([OH:6])[CH:8]=3)=[CH:21][N:22]([C@H:30]3[CH2:31][CH2:32][C@H:33]([N:36]4[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH2:41]4)[CH2:34][CH2:35]3)[C:23]=2[N:24]=[CH:25][N:26]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of trans-5-(3-methoxy-4-phenoxyphenyl)-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine acetate (50 mg, 0.098 mmol) in 48% aqueous hydrobromic acid (1 mL) was heated at 120° C. for 2 hours. The solution was cooled and concentrated under reduced pressure then purified by preparative RP-HPLC to give trans-5-{4-amino-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-2-phenoxyphenol (32 mg, 66%): 1H NMR (DMSO-d6, 400 MHz) δ 9.8(bs, 1H), 8.13(s, 1H), 7.39(s, 1H), 7.31(t, 2H), 7.03(m, 3H), 6.89(m, 3H), 6.17(bs, 2H), 4.55(m, 1H), 2.2-2.6(m, 9H), 2.15(s, 3H), 1.8-2.2(m, 6H), 1.44 (m, 2H); MS MH+499.4; RP-HPLC (Hypersil HS, 5 μm, 100 A 4.6×250 mm; 25%-100% acetonitrile—0.05 M ammonium acetate over 10 min, 1 ml/min) tr 13.47 min.

Workup

temperatureThe solution was cooled
concentrationconcentrated under reduced pressure
customthen purified by preparative RP-HPLC

Sources & evidence

ORD record: ord-ef79c6a435174270becb91e235f26723
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713474B2

Reaction notes

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