Hydrochloric Acid → HCID 59023729, compound

HRID 1678216Notes

Reaction equation

HRID 1678216 reaction equation
Cl.[S:2]1[C:6]([C:7]2[CH:8]=[C:9]([N:16]([CH2:24][CH2:25][CH2:26][O:27][Si](C(C)(C)C)(C)C)[C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[N:18]=3)[CH:10]=[C:11]3[C:15]=2[NH:14][N:13]=[CH:12]3)=[CH:5][C:4]2[CH:35]=[CH:36][CH:37]=[CH:38][C:3]1=2>C(O)C>[NH2:23][C:19]1[N:18]=[C:17]([N:16]([C:9]2[CH:10]=[C:11]3[C:15](=[C:7]([C:6]4[S:2][C:3]5[CH:38]=[CH:37][CH:36]=[CH:35][C:4]=5[CH:5]=4)[CH:8]=2)[NH:14][N:13]=[CH:12]3)[CH2:24][CH2:25][CH2:26][OH:27])[CH:22]=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59024051HCID 59024051, compound

Product 1

HCID 59023729HCID 59023729, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

6N hydrochloric acid (1 mL) was added to a mixture of N4-(7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-N4-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrimidine-2,4-diamine (prepared from example #F.8.1, via general procedures O then N, 0.179 g, 0.339 mmol) in ethanol (2 mL). The reaction mixture was heated to about 65° C. for about 1 hour then cooled to about ambient temperature. The solvents were evaporated and the residue was purified by reverse phase chromatography (Thermo Hypersil-Keystone 250×21.2 mm 8μ Hypersil® HS C18 column; 5% acetonitrile/0.1 M aqueous ammonium acetate −100% acetonitrile over 20 min, 100% acetonitrile hold 5 minutes, 21 mL/min) to afford (3-[(2-amino-pyrimidin-4-yl)-(7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-amino]-propan-1-ol (0.022 g, 0.053 mmol) as an off white solid; RP-HPLC (Table 1, Method e) Rt 1.77 min.; m/z: (M+H)+ 417.1.

Workup

  1. customprepared from example #F.8.1, via general procedures O
  2. temperaturethen cooled to about ambient temperature
  3. customThe solvents were evaporated
  4. customthe residue was purified by reverse phase chromatography (Thermo Hypersil-Keystone 250×21.2 mm 8μ Hypersil® HS C18 column; 5% acetonitrile/0.1 M aqueous ammonium acetate −100% acetonitrile over 20 min, 100% acetonitrile hold 5 minutes, 21 mL/min)

Sources & evidence

ORD record
ord-a34412e8484c4406a4123e7c8e1b761e
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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