Sulfanilamide → 4-(4-(4-(Aminomethyl)piperidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)benzenesulfonamide

HRID 1038806Notes

Reaction equation

HRID 1038806 reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:16]3[O:34][CH:33]=[CH:32][C:17]=3[N:18]=[C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([S:28](=[O:31])(=[O:30])[NH2:29])=[CH:24][CH:23]=3)[N:20]=2)[CH2:11][CH2:10]1)(C)(C)C.ClC1N=C(Cl)C2OC=CC=2N=1.C(OC(NCC1CCNCC1)=O)(C)(C)C.NC1C=CC(S(N)(=O)=O)=CC=1.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[NH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:16]3[O:34][CH:33]=[CH:32][C:17]=3[N:18]=[C:19]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([S:28]([NH2:29])(=[O:31])=[O:30])=[CH:26][CH:27]=3)[N:20]=2)[CH2:11][CH2:10]1

Participants

6

Reactant 5

HCID 5333SulfanilamideHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 21863450Trifluoroacetic acid methylene chlorideHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidineHCID 70143000Tert-butyl(1-(2-(4-sulfamoylphenylamino)furo[3,2-d]pyrimidin-4-yl)piperidin-4-yl)methylcarbamate

Product 1

HCID 687508444-(4-(4-(Aminomethyl)piperidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)benzenesulfonamideYield 63%

Procedure

To a flask containing tert-butyl(1-(2-(4-sulfamoylphenylamino)furo[3,2-d]pyrimidin-4-yl)piperidin-4-yl)methylcarbamate (0.215 g, 0.428 mmol, prepared using A from 2,4-dichlorofuro[3,2-d]pyrimidine [ArkPharm] with 4-(tert-butoxycarbonylaminomethyl)piperidine [Tyger] and B with 4-aminobenzenesulfonamide) was slowly added a 20% TFA/DCM (3 mL) solution. The mixture was stirred at rt for about 4 h. The solvent was removed in vacuo and the residue purified by reverse phase preparatory HPLC (Table 2, method b) to provide 4-(4-(4-(aminomethyl)piperidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)benzenesulfonamide (0.142 g, 63%): LC/MS (Table 2, Method a) Rt=0.20 min; MS m/z 403.2 (M+H)+. Syk IC50=A

Workup

  1. customprepared
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by reverse phase preparatory HPLC (Table 2, method b)

Sources & evidence

ORD record
ord-9bc5b0696e7f4b88b85ef5cff72ab9fe
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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