Dichloromethane → HCID 58346581, compound

HRID 222023Notes

Reaction equation

HRID 222023 reaction equation
C(Cl)Cl.[Cl:4][C:5]1[CH:6]=[C:7]([NH:20][C:21]2[C:26]3[C:27]4[CH2:35][CH2:34][C:33]5[N:32]([CH2:36][CH2:37]O)[N:31]=[CH:30][C:29]=5[C:28]=4[S:39][C:25]=3[N:24]=[CH:23][N:22]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1.S(Br)([Br:42])=O>O>[Br:42][CH2:37][CH2:36][N:32]1[C:33]2[CH2:34][CH2:35][C:27]3[C:26]4[C:25](=[N:24][CH:23]=[N:22][C:21]=4[NH:20][C:7]4[CH:8]=[CH:9][C:10]([O:11][CH2:12][C:13]5[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=5)=[C:5]([Cl:4])[CH:6]=4)[S:39][C:28]=3[C:29]=2[CH:30]=[N:31]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 68176Thionyl bromideHCID 57600143HCID 57600143, compound

Product 1

HCID 58346581HCID 58346581, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10 mL CH2Cl2 cooled to 0° C. was added 2-[6-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-4,5-dihydro-3H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-3-yl]ethanol (295 mg, 0.57 mmol) followed by thionyl bromide (0.11 mL, 1.41 mmol), and the contents allowed to stir with warming to rt. After 4 h stirring at rt, the contents were diluted with H2O (10 mL). The layers were separated and the aqueous layer extracted with CH2Cl2 (3×10 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was triturated from methanol to afford the final product (205 mg, 62%) as an off-white solid. 1H-NMR (DMSO-d6) δ 3.09 (t, 2H), 3.39 (t, 2H), 3.85 (m, 2H), 4.52 (m, 2H), 5.24 (s, 2H), 7.14-7.34 (m, 4H), 7.40-7.53 (m, 2H), 7.75 (s, 1H), 7.79 (d, 1H), 8.35 (s, 1H), 8.40 (s, 1H); LCMS RT=3.82 min; [M+H]+=584.0, 586.0.

Workup

  1. stirringAfter 4 h stirring at rt
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with CH2Cl2 (3×10 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was triturated from methanol

Sources & evidence

ORD record
ord-02154b9e69c74efc961cfd1ce032ff4d
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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