Triethylamine → HCID 59490308, compound

HRID 1808032Notes

Reaction equation

HRID 1808032 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]2[N:14]=[C:13]([NH:22][C:23]3[CH:24]=[C:25]([CH2:29][CH2:30][OH:31])[CH:26]=[CH:27][CH:28]=3)[N:12]=[CH:11][C:10]=2[CH2:9]1.C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>ClCCl>[CH3:39][S:40]([O:31][CH2:30][CH2:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([NH:22][C:13]2[N:12]=[CH:11][C:10]3[CH2:9][C@@H:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[C:15]=3[N:14]=2)[CH:24]=1)(=[O:42])=[O:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59489874HCID 59489874, compound

Product 1

HCID 59490308HCID 59490308, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-(3-(6-(2-fluorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenyl)ethanol (4.59 g, 11.17 mmol) in dichloromethane (50 mL) was added triethylamine (2.33 mL, 16.75 mmol) and methanesulfonyl chloride (0.95 mL, 12.28 mmol). The mixture was stirred at room temperature for 1 h, washed with water (60 mL×3), dried over sodium sulfate and concentrated to yield the title compound as a yellow solid (5.37 g, 98% yield). 1H-NMR (DMSO-d6) δ 9.59 (s, 1 H), 8.37-8.35 (dd, 1 H), 8.33 (s, 1 H), 7.80 (s, 1 H), 7.71 (d, J=10.4 Hz, 1 H), 7.54-7.45 (m, 2 H), 7.29-7.22 (m, 3 H), 7.07-7.02 (m, 2 H), 6.82-6.78 (m, 2 H), 4.67 (t, J=6.8 Hz, 1 H), 4.45 (t, J=6.8 Hz, 2 H), 3.22-3.08 (m, 2 H), 3.13 (s, 3 H), 3.01 (t, J=6.4 Hz, 2 H). LCMS m/e 490 [M+H].

Workup

  1. washwashed with water (60 mL×3)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bef9a7edb5ff44a59d5cc2d25cabe112
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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