Triethylamine → HCID 49780577, compound

HRID 929512Notes

Reaction equation

HRID 929512 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)=[O:9])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:29][N:30]([CH3:45])[C:31]1[CH:40]=[CH:39][CH:38]=[C:37]2[C:32]=1[CH:33]=[CH:34][CH:35]=[C:36]2[S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[CH3:29][N:30]([CH3:45])[C:31]1[CH:40]=[CH:39][CH:38]=[C:37]2[C:32]=1[CH:33]=[CH:34][CH:35]=[C:36]2[S:41]([N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:13][CH:12]=2)=[O:9])[CH2:3][CH2:2]1)(=[O:43])=[O:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11801Dansyl chlorideHCID 49780164HCID 49780164, compound

Product 1

HCID 49780577HCID 49780577, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 42 (200 mg, 0.7 mmol) was dissolved in DCM (7 mL) and triethylamine (100 μL, 0.7 mmol) added followed by 5-(dimethylamino)-1-naphthalenesulfonyl chloride (207 mg, 0.77 mmol). The reaction was evaporated, reconstituted in EtOAc and washed with 1N HCl and 1N K2CO3. Flash chromatography eluted with 2:1 EtOAc:hexanes afforded compound 59 (338 mg, 93%) as a tan solid: Mp 102-107° C. 1H NMR (500 MHz, DMSO-d6□ 8.52 (d, J=8.5 Hz, 1H), 8.45 (s, 1H), 8.28 (d, J=8.7 Hz, 1H), 8.14 (d, J=7.3 Hz, 1H), 7.67 (t, J=7.5 Hz, 1H), 7.62 (t, J=8.1 Hz, 1H), 7.43 (d, J=9.1 Hz, 2H), 7.28 (d, J=7.5 Hz, 1H), 7.19 (d, J=8.7 Hz, 2H), 6.24 (d, J=7.5 Hz, 1H), 3.60-3.53 (m, 3H), 2.88 (t, J=10.5 Hz, 2H, obscured by s δ 2.84), 2.84 (s, 6H), 1.84 (dd, J=12.9, 3.0 Hz, 2H), 1.38 (dq, J=10.6, 3.6 Hz, 2H). Purity 97%. HRMS calculated for C25H27F3N4O4S+H+ 537.1783. found (ESI(+), [M+H]) 537.1785.

Workup

  1. customThe reaction was evaporated
  2. washwashed with 1N HCl and 1N K2CO3
  3. washFlash chromatography eluted with 2:1 EtOAc

Sources & evidence

ORD record
ord-6229582cc38e477095ad7d3297e6574f
Source dataset
uspto-grants-2016_03
Patent number
US09296693B2

Reaction notes

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