Triethylamine → HCID 59161219, compound

HRID 545549Notes

Reaction equation

HRID 545549 reaction equation
Cl.[NH2:2][CH:3]1[CH2:15][CH2:14][C:13]2[N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[C:11]3[CH:10]=[CH:9][C:8]([C:24]#[N:25])=[CH:7][C:6]=3[C:5]=2[CH2:4]1.C(N(CC)CC)C.[CH:33]1([S:36](Cl)(=[O:38])=[O:37])[CH2:35][CH2:34]1>ClCCl>[C:24]([C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)[C:13]1[CH2:14][CH2:15][CH:3]([NH:2][S:36]([CH:33]3[CH2:35][CH2:34]3)(=[O:38])=[O:37])[CH2:4][C:5]2=1)#[N:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 57431673HCID 57431673, compound

Product 1

HCID 59161219HCID 59161219, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine 6-amino-9-(3-fluoro-benzyl)6,7,8,9-tetrahydro-5H-carbazole-3-carbonitrile, hydrochloride salt (Preparation 54) (125 mg, 0.35 mmol) and triethylamine (0.195 mL, 1.4 mmol) in dichloromethane (3 mL) under nitrogen. Add cyclopropylsulfonylchloride (51 mg, 0.36 mmol) in dichloromethane (1 mL). Stir for 18 h at room temperature. Purify the reaction solution directly by flash chromatography, eluting with 20% ethyl acetate/hexane and then a gradient up to 50% ethyl acetateihexane to obtain 80 mg. Triturate in diethyl ether to obtain 61 mg (41%) of a tan solid. MS (ES): m/z 424 (M+1), 422 (M−1); 1H NMR(DMSO-d6): δ 7.98 (d, 1H, J=1.3 Hz), 7.56 (d, 1H, J=8.4 Hz), 7.41 (dd, 1H, J=8.4, 1.3 Hz), 7.36-7.30 (m, 2H), 7.07 (dt, 1H, J=8.7, 2.5 Hz), 6.88 (d, 1H, J=9.7 Hz), 6.83 (d, 1H, J=7.9 Hz), 5.42 (d, 2H, J=5.3 Hz), 3.68 (m, 1H), 3.10 (dd, 1H, J=15.4, 5.3 Hz), 2.90-2.81 (m, 1H), 2.79-2.61 (m, 3H), 2.13 (m, 1H), 1.86 (m, 1H), 0.98-0.91 (m, 4H).

Workup

  1. customPurify the reaction solution directly by flash chromatography
  2. washeluting with 20% ethyl acetate/hexane
  3. customa gradient up to 50% ethyl acetateihexane to obtain 80 mg
  4. customTriturate in diethyl ether

Sources & evidence

ORD record
ord-54b59812623e4bb6b2eacb95780c05aa
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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