Chloroacetyl chloride → HCID 58346586, compound

HRID 222049Notes

Reaction equation

HRID 222049 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[N:19]=[CH:20][N:21]=[C:22]3[S:39][C:25]4[C:26]5[C:30]([CH2:31][CH2:32][C:24]=4[C:23]=23)=[N:29][N:28]([CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:27]=5)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.[Cl:40][CH2:41][C:42](Cl)=[O:43].C(N(CC)CC)C>C(Cl)Cl.O>[Cl:40][CH2:41][C:42]([N:36]1[CH2:37][CH2:38][CH:33]([N:28]2[CH:27]=[C:26]3[C:30]([CH2:31][CH2:32][C:24]4[C:23]5=[C:18]([NH:17][C:4]6[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]7[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=7)=[C:2]([Cl:1])[CH:3]=6)[N:19]=[CH:20][N:21]=[C:22]5[S:39][C:25]=43)=[N:29]2)[CH2:34][CH2:35]1)=[O:43]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 58346593HCID 58346593, compound

Product 1

HCID 58346586HCID 58346586, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-2-piperidin-4-yl-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-6-amine 500 mg (0.89 mmol, 1 eq) in DCM (10 mL) was added chloroacetyl chloride (100 mg, 0.89 mmol, 1 eq) and triethylamine (90 mg, 0.89 mmol, 1 eq). It was stirred at rt for 3 h after which time it was diluted with water. It was then was extracted 3 times with EtOAc. The combined organic layers were dried over MgSO4 and concentrated to yield the desired product (400 mg, 70%). 1H-NMR (DMSO-d6) δ 8.45 (broad, 1H), 8.33 (s, 1H), 8.04 (s, 1H), 7.74 (d, 1H), 7.5 (dd, 1H), 7.44 (m, 1H), 7.29 (m, 2H), 7.20 (m, 2H), 5.23 (s, 2H), 4.45 (m, 4H), 3.93 (m, 1H), 3.38 (t, 2H), 3.24 (m, 1H), 2.92 (t, 2H), 2.83 (m, 1H), 2.08 (m, 2H), 1.97 (m, 1H), 1.80 (m, 1H). LCMS RT=3.68 min; [M+H]+=637.4.

Workup

  1. extractionIt was then was extracted 3 times with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-809abe1a71fc4fa3832b330a48259055
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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