1-Hydroxybenzotriazole → HCID 58171615, compound

HRID 1752327Notes

Reaction equation

HRID 1752327 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([CH:14]3[CH2:18][CH2:17][N:16]([C:19]([O:21][CH:22]4[CH:29]5[CH2:30][C:25]6([C:32](O)=[O:33])[CH2:26][CH:27]([CH2:31][CH:23]4[CH2:24]6)[CH2:28]5)=[O:20])[CH2:15]3)=[N:12][CH:13]=2)=[CH:4][C:3]1=[O:35].C1C=CC2N(O)N=[N:42]C=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>ClCCl>[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([CH:14]3[CH2:18][CH2:17][N:16]([C:19]([O:21][CH:22]4[CH:23]5[CH2:24][C:25]6([C:32](=[O:33])[NH2:42])[CH2:26][CH:27]([CH2:28][CH:29]4[CH2:30]6)[CH2:31]5)=[O:20])[CH2:15]3)=[N:12][CH:13]=2)=[CH:4][C:3]1=[O:35]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58171490HCID 58171490, compound

Product 1

HCID 58171615HCID 58171615, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-((3-(5-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)pyrimidin-2-yl)pyrrolidine-1-carbonyl)oxy)adamantane-1-carboxylic acid (20 mg, 0.04 mmol), HOBt (11.3 mg, 0.08 mmol), EDCl (16.5 mg, 0.08 mmol) and i-Pr2NEt (27 mg, 0.21 mmol) in dichloromethane (5 mL) was stirred overnight under ammonia gas. The reaction mixture was concentrated to afford an oil which was purified by basic preparative HPLC to afford two isomers:

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto afford an oil which
  3. customwas purified by basic preparative HPLC
  4. customto afford two isomers

Sources & evidence

ORD record
ord-d8ca9068b21f404abae38ed434e8638b
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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