Ethylenediamine → HCID 71254703, compound

HRID 540284Notes

Reaction equation

HRID 540284 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[O:5]=[S:6]1(=[O:32])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][N:9]([C:17]2[CH:26]=[C:25]([S:27](Cl)(=[O:29])=[O:28])[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([CH3:31])[CH:23]=3)[N:18]=2)[CH2:8][CH2:7]1>ClCCl.C(N(CC)CC)C>[NH2:3][CH2:2][CH2:1][NH:4][S:27]([C:25]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH3:31])[CH:23]=2)[N:18]=[C:17]([N:9]2[CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[S:6](=[O:32])(=[O:5])[CH2:7][CH2:8]2)[CH:26]=1)(=[O:28])=[O:29]

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 86691431HCID 86691431, compound

Product 1

HCID 71254703HCID 71254703, compoundYield 3.1%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of ethane-1,2-diamine (320 mg, 5.4 mmol) in dichloromethane (50 mL) was added triethylamine (3 drops) followed by 2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinoline-4-sulfonyl chloride (the filtrate from the above step) at 0° C. The resulting mixture was stirred at room temperature for 16 hours and concentrated in vacuo. The residue was purified by preparative HPLC to afford 56.38 mg of the desired product (yield of three steps was 3.1%). MS (ESI+) [(M+H)+] 461, 1H NMR (400 MHz, CD3OD) δ ppm 8.11 (s, 1 H), 7.99-7.97 (d, J=8.4 Hz, 1 H), 7.85-7.83 (d, J=7.6 Hz, 1 H), 7.67-7.63 (m, 3 H), 7.49-7.45 (m, 2 H), 5.25 (s, 2 H), 4.76-4.03 (m, 2 H), 3.63-3.59 (t, 2 H), 3.03-3.00 (m, 4 H), 2.46 (s, 3 H).

Workup

  1. customat 0° C
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-0b7d1af2230347d1884a47a7732e0af5
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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