Formic Acid → HCID 59024003, compound

HRID 1678230Notes

Reaction equation

HRID 1678230 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][N:14]([C:33]1[CH:38]=[CH:37][N:36]=[C:35]([NH2:39])[N:34]=1)[C:15]1[CH:16]=[C:17]2[C:21](=[C:22]([C:24]3[S:28][C:27]4[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=4[CH:25]=3)[CH:23]=1)[NH:20][N:19]=[CH:18]2)C1C=CC=CC=1.C(O)=O>CO.[Pd]>[NH2:10][CH2:11][CH2:12][CH2:13][N:14]([C:15]1[CH:16]=[C:17]2[C:21](=[C:22]([C:24]3[S:28][C:27]4[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=4[CH:25]=3)[CH:23]=1)[NH:20][N:19]=[CH:18]2)[C:33]1[CH:38]=[CH:37][N:36]=[C:35]([NH2:39])[N:34]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 59024164HCID 59024164, compound

Product 1

HCID 59024003HCID 59024003, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of {3-[(2-amino-pyrimidin-4-yl)-(7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-amino]-propyl}-carbamic acid benzyl ester (prepared from Example #F.8.1 using general procedures O and N, 0.169 g, 0.308 mmol) and formic acid (0.116 mL, 3.08 mmol) in methanol (2 mL) was added dropwise to a suspension of Palladium black (0.080 g, 0.752 mmol) in methanol (1.5 mL). The resulting mixture was allowed to stir at ambient temperature for about 19 hours. The resulting suspension was filtered though celite and the solvent was removed under reduced pressure. The resulting crude product was purified by reverse 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 N4-(3-amino-propyl)-N4-(7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-pyrimidine-2,4-diamine (0.021 g, 17% yield) as a green solid. RP-HPLC (Table 1, Method e) Rt 1.62 min.; m/z: (M+H)+ 416.1.

Workup

  1. filtrationThe resulting suspension was filtered though celite
  2. customthe solvent was removed under reduced pressure
  3. customThe resulting crude product was purified by reverse 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-6fbca47824c2478b8f8848e94736f65d
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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