Hydrochloric Acid → HCID 178434340, compound

HRID 1038832Notes

Reaction equation

HRID 1038832 reaction equation
C([NH:4][CH2:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[C:12]3[O:37][CH:36]=[CH:35][C:13]=3[N:14]=[C:15]([NH:17][C:18]3[CH:26]=[C:25]4[C:21]([C:22]([CH3:34])=[N:23][N:24]4C(OC(C)(C)C)=O)=[CH:20][CH:19]=3)[N:16]=2)[CH2:7]1)(=O)C.Cl.NCC1CCN(C(OC(C)(C)C)=O)C1.C(Cl)(=O)C.ClC1N=C(Cl)C2OC=CC=2N=1.Cl>CO>[NH2:4][CH2:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[C:12]3[O:37][CH:36]=[CH:35][C:13]=3[N:14]=[C:15]([NH:17][C:18]3[CH:26]=[C:25]4[C:21]([C:22]([CH3:34])=[N:23][NH:24]4)=[CH:20][CH:19]=3)[N:16]=2)[CH2:7]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 45072187tert-Butyl 3-(aminomethyl)pyrrolidine-1-carboxylate--hydrogen chloride (1/1)HCID 457899682,4-Dichlorofuro[3,2-D]pyrimidineHCID 67130041HCID 67130041, compound

Product 1

HCID 178434340HCID 178434340, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of tert-butyl 6-(4-(3-(acetamidomethyl)pyrrolidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-3-methyl-1H-indazole-1-carboxylate (0.57 g, 1.1 mmol, prepared using E.1 from tert-butyl 3-(aminomethyl)pyrrolidine-1-carboxylate hydrochloride [Astatech] with acetyl chloride, C, A with 2,4-dichlorofuro[3,2-d]pyrimidine [ArkPharm] and B with Example #3, Step B) in MeOH (12 mL) was added concentrated HCl (12 mL). The mixture was stirred for about 32 h at about 90° C. The mixture was cooled to rt, and a white precipitate formed that was collected by vacuum filtration and washed with water. The solid was dissolved in hot aqueous 1 M HCl and the suspension was filtered while hot. To the filtrate was added aqueous NH4OH to reach a pH˜9, and the resulting precipitate was collected to give 4-(3-(aminomethyl)pyrrolidin-1-yl)-N-(3-methyl-1H-indazol-6-yl)furo[3,2-d]pyrimidin-2-amine (0.27 g, 61%): LC/MS (Table 2, Method h) Rt=1.61 min; MS m/z: 364 (M+H)+. Syk IC50=A

Workup

  1. temperatureThe mixture was cooled to rt
  2. customa white precipitate formed
  3. filtrationthat was collected by vacuum filtration
  4. washwashed with water
  5. dissolutionThe solid was dissolved in hot aqueous 1 M HCl
  6. filtrationthe suspension was filtered while hot
  7. additionTo the filtrate was added aqueous NH4OH
  8. customthe resulting precipitate was collected

Sources & evidence

ORD record
ord-c2b96bd7d9d049508eee901b9dcc75f3
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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