Tert-butyl (1-(4-(1-(cyanomethyl)-6-oxo-8-phenyl-1,6-dihydropyrano[3,2-g]indazol-7-yl)phenyl)cyclobutyl)carbamate → 2-(7-(4-(1-aminocyclobutyl)phenyl)-6-oxo-8-phenylpyrano[3,2-g]indazol-1(6H)-yl)acetonitrile

HRID 1037413Notes

Reaction equation

HRID 1037413 reaction equation
[C:1]([CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]3[C:16](=[O:17])[C:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5([NH:28]C(=O)OC(C)(C)C)[CH2:27][CH2:26][CH2:25]5)=[CH:20][CH:19]=4)=[C:14]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[O:13][C:11]3=2)[CH:6]=[N:5]1)#[N:2]>CO>[NH2:28][C:24]1([C:21]2[CH:20]=[CH:19][C:18]([C:15]3[C:16](=[O:17])[C:10]4[C:11]([O:13][C:14]=3[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[C:12]3[C:7]([CH:6]=[N:5][N:4]3[CH2:3][C:1]#[N:2])=[CH:8][CH:9]=4)=[CH:23][CH:22]=2)[CH2:27][CH2:26][CH2:25]1

Participants

3

Reactant 1

HCID 86671057Tert-butyl (1-(4-(1-(cyanomethyl)-6-oxo-8-phenyl-1,6-dihydropyrano[3,2-g]indazol-7-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 682273232-(7-(4-(1-aminocyclobutyl)phenyl)-6-oxo-8-phenylpyrano[3,2-g]indazol-1(6H)-yl)acetonitrileYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

tert-Butyl (1-(4-(1-(cyanomethyl)-6-oxo-8-phenyl-1,6-dihydropyrano[3,2-g]indazol-7-yl)phenyl)cyclobutyl)carbamate (20 mg, 0.037 mmol) was loaded in a 1 g SCX-2 cartridge column preconditioned with methanol (2×1 mL). The compound was loaded to the column using 1 mL of methanol. After 1 h the column was washed with 3×1 mL of methanol. The product was eluted with 7 N ammonia in methanol (2×1 mL). The solvent was evaporated to afford the title compound (6 mg, 49%). Residual starting material was recovered from MeOH washed (10 mg). 1H NMR (500 MHz, MeOD): δ 8.19 (br s, 1H), 8.06 (d, J=8.6 Hz, 1H), 7.71 (d, J=8.3 Hz, 1H), 7.50-7.47 (m, 2H), 7.40-7.30 (m, 5H), 7.25-7.20 (m, 2H), 5.65 (s, 2H) 5.12 (s, 1H, NH) 2.64-2.56 (m, 4H), 2.30-2.22 (m, 1H), 2.04-1.94 (m, 1H). LCMS (Method J): RT=0.92 min, [M+H]+=448.

Workup

  1. washAfter 1 h the column was washed with 3×1 mL of methanol
  2. washThe product was eluted with 7 N ammonia in methanol (2×1 mL)
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9d1fa60c8fe542e8a53453da5a360c0f
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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