Hydrochloric Acid → HCID 58346439, compound

HRID 222041Notes

Reaction equation

HRID 222041 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:17]=[CH:18][N:19]=[C:20]3[S:41][C:23]4[C:24]5[C:28]([CH2:29][CH2:30][C:22]=4[C:21]=23)=[N:27][N:26]([CH2:31][CH2:32][O:33][Si](C(C)(C)C)(C)C)[CH:25]=5)=[CH:11][C:10]=1[Cl:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:21]3[C:22]4[CH2:30][CH2:29][C:28]5[C:24](=[CH:25][N:26]([CH2:31][CH2:32][OH:33])[N:27]=5)[C:23]=4[S:41][C:20]=3[N:19]=[CH:18][N:17]=2)=[CH:11][C:10]=1[Cl:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58346459HCID 58346459, compound

Product 1

HCID 58346439HCID 58346439, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred and cooled (0° C.) solution of N-[4-(benzyloxy)-3-chlorophenyl]-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-6-amine (1673 mg, 2.7 mmol) in THF (55 mL) was added aq. HCl (2M, 1.6 mL). The resulting clear solution slowly became heterogeneous with a yellow precipitate. The mixture was warmed to rt over a 5 h period, after which time the solvent was removed in vacuo. The crude residue was diluted with EtOAc (5 mL) and aq. Na2CO3 (2M, 100 mL) to attain a pH=11 solution which was vigorously stirred for 1 h. The contents were filtered to a light yellow solid, which was washed with water (400 mL), and then hexanes (500 mL). The collected product was dried under vacuum, to afford the final product (817 mg, 60%) as a light yellow solid. 1H-NMR (DMSO-d6) δ 8.41 (s, 1H), 8.34 (s, 1H), 7.93 (s, 1H), 7.75 (d, 1H), 7.33-7.53 (m, 6H), 7.23 (s, 1H), 5.21 (s, 2H), 4.92 (t, 1H), 4.10 (t, 2H), 3.73 (td, 2H), 3.38 (t, 2H), 2.92 (t, 2H); LCMS RT=3.56 min; [M+H]+=504.2.

Workup

  1. customafter which time the solvent was removed in vacuo
  2. additionThe crude residue was diluted with EtOAc (5 mL) and aq. Na2CO3 (2M, 100 mL)
  3. stirringwas vigorously stirred for 1 h
  4. filtrationThe contents were filtered to a light yellow solid, which
  5. washwas washed with water (400 mL)
  6. customThe collected product was dried under vacuum

Sources & evidence

ORD record
ord-348796555a114a35a9b7a9c175d2f4ea
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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