Dichloromethane → HCID 58346437, compound

HRID 222032Notes

Reaction equation

HRID 222032 reaction equation
C(Cl)Cl.[Cl:4][C:5]1[CH:6]=[C:7]([NH:19][C:20]2[C:25]3[C:26]4[CH2:34][CH2:33][C:32]5[C:28](=[CH:29][N:30]([CH2:35][CH2:36]O)[N:31]=5)[C:27]=4[S:38][C:24]=3[N:23]=[CH:22][N:21]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.S(Br)([Br:41])=O>O>[Br:41][CH2:36][CH2:35][N:30]1[CH:29]=[C:28]2[C:32]([CH2:33][CH2:34][C:26]3[C:25]4=[C:20]([NH:19][C:7]5[CH:8]=[CH:9][C:10]([O:11][CH2:12][C:13]6[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=6)=[C:5]([Cl:4])[CH:6]=5)[N:21]=[CH:22][N:23]=[C:24]4[S:38][C:27]=32)=[N:31]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 68176Thionyl bromideHCID 58346552HCID 58346552, compound

Product 1

HCID 58346437HCID 58346437, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 60 mL CH2Cl2 cooled to 0° C. was added 2-(6-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-2-yl)ethanol (1.60 g, 3.2 mmol), followed by thionyl bromide (2.31 g, 11.1 mmol). The contents were then stirred with warming to it over a 24 h period, after which time water (5 mL) was added to quench the reaction mixture. The solvent was removed under reduced pressure. The crude residue was diluted with aq. 2M Na2CO3 and vigorously stirred for 1 h. The precipitate was collected by filtration and triturated with methanol (30 mL) to afford the desired product (1.70 g, 94%) as a light-brown solid. 1H-NMR (DMSO-d6) δ 8.59 (d, 1H), 8.41 (s, 1H), 8.36 (s, 1H), 8.01 (s, 1H), 7.82 (dd, 1H), 7.78 (s, 1H), 7.47-7.60 (m, 2H), 7.30 (dd, 1H), 7.19 (d, 1H), 5.27 (s, 2H), 4.42 (t, 2H), 3.82 (t, 2H), 3.38 (t, 2H), 2.90 (t, 2H); LCMS RT=2.89 min; [M+H]+=567.4.

Workup

  1. temperaturewith warming to it over a 24 h period
  2. customto quench the reaction mixture
  3. customThe solvent was removed under reduced pressure
  4. additionThe crude residue was diluted with aq. 2M Na2CO3
  5. stirringvigorously stirred for 1 h
  6. filtrationThe precipitate was collected by filtration
  7. customtriturated with methanol (30 mL)

Sources & evidence

ORD record
ord-dfc0381275ec4c548dd713c49b8b2b39
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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