Hydrochloric Acid → HCID 58346526, compound

HRID 222021Notes

Reaction equation

HRID 222021 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][C:16]3[C:22]4=[C:23]([NH:27][C:28]5[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]6[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=6)=[C:30]([Cl:43])[CH:29]=5)[N:24]=[CH:25][N:26]=[C:21]4[S:20][C:17]=32)=[N:12]1)(C(C)(C)C)(C)C.Cl>C1COCC1>[Cl:43][C:30]1[CH:29]=[C:28]([NH:27][C:23]2[C:22]3[C:16]4[CH2:15][CH2:14][C:13]5[C:18](=[CH:19][N:11]([CH2:10][CH2:9][OH:8])[N:12]=5)[C:17]=4[S:20][C:21]=3[N:26]=[CH:25][N:24]=2)[CH:33]=[CH:32][C:31]=1[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58346452HCID 58346452, compound

Product 1

HCID 58346526HCID 58346526, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 250 mL THF cooled to 0° C. was added 2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-6-amine (7.70 g, 10.9 mmol). To the homogeneous mixture was then added aq HCl 2M, 6.5 mL), upon which the contents darken. The contents were stirred with warming to rt over a 4 h period, after which time the solvent was removed under reduced pressure. The crude residue was diluted with aq Na2CO3 (2M, 100 mL) to attain a pH=11 solution which was vigorously stirred, and the contents then filtered to a light brown solid which was dried under hi-vac. The collected product was triturated two times from hot ethanol to afford the final product (5.05 g, 89%) as a light tan solid. 1H-NMR (DMSO-d6) δ 2.90 (t, 2H), 3.36 (t, 2H), 3.72 (m, 2H), 4.06 (t, 2H), 4.90 (s, 1H), 5.24 (s, 2H), 7.14-7.34 (m, 4H), 7.41-7.54 (m, 2H), 7.78 (d, 1H), 7.95 (s, 1H), 8.35 (s, 1H), 8.40 (s, 1H); LCMS RT=3.39 min; [M+H]+=522.2.

Workup

  1. customafter which time the solvent was removed under reduced pressure
  2. additionThe crude residue was diluted with aq Na2CO3 (2M, 100 mL)
  3. stirringwas vigorously stirred
  4. filtrationthe contents then filtered to a light brown solid which
  5. customwas dried under hi-vac
  6. customThe collected product was triturated two times from hot ethanol

Sources & evidence

ORD record
ord-7ba264d009614675a553e830e2dc2700
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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