1-Hydroxybenzotriazole → HCID 10128584, compound

HRID 1893847Notes

Reaction equation

HRID 1893847 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@H:22]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:23]([NH2:25])=[O:24])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][NH:20][CH3:21])=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH:30]N1C2C=CC=CC=2N=N1.Cl.[CH3:41][N:42]([CH3:51])[CH2:43][CH2:44]CN=C=NCC>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C@H:22]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:23]([NH2:25])=[O:24])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][N:20]([C:44](=[O:30])[CH2:43][N:42]([CH3:51])[CH3:41])[CH3:21])=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67197669HCID 67197669, compound

Product 1

HCID 10128584HCID 10128584, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(2R)-2-[N-(4-Chlorobenzenesulfonyl)-N-(4-methylaminomethyl-benzyl)-amino]-4-methyl-pentanoic acid amide (75 mg, 0.17 mmol), (α-dimethylamino)acetic acid (18 mg, 0.17 mmol), 1-hydroxybenzotriazole (24 mg, 0.17 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (33 mg, 0.17 mmol) were combined in 3 mL CH2Cl2 and stirred overnight. The reaction mixture was diluted with 5 mL CH2Cl2 and washed with 1 N NaOH and brine. The organic phase was dried by filtering through cotton and the solvent was removed in vacuo. Purification via preparative HPLC afforded the title compound (61 mg) in 68% yield. MS (ESI), 523.4 (M+H)+1H NMR (CDCl3) δ 8.02 (d, 2H, J=8.0), 7.71 (d, 2H, J=8.0), 7.37 (d, 2H, J=8.0), 7.28 (d, 2H, J=8.0), 6.23 (br s, 1H), 5.51 (br s, 1H), 4.46 (s, 2H), 4.70 (d, 1H, Jab=16), 4.33 (d, 1H, Jab=16), 3.25 (t, 1H, J=6.0), 2.69 (s, 3H), 2.63 (s, 2H), 2.20 (s, 6H), 1.95 (m, 1H), 1.60 (m, 2H), 0.98 (d, 3H, J=7.0), 0.94 (d, 3H, J=7.0).

Workup

  1. washwashed with 1 N NaOH and brine
  2. customThe organic phase was dried
  3. filtrationby filtering through cotton
  4. customthe solvent was removed in vacuo
  5. customPurification via preparative HPLC

Sources & evidence

ORD record
ord-646a788f86a8492598ea951cf3277ad6
Source dataset
uspto-grants-2013_08
Patent number
US08513253B2

Reaction notes

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