1-Hydroxybenzotriazole → HCID 67453273, compound

HRID 869156Notes

Reaction equation

HRID 869156 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[N:13][C:14]([NH:17][CH2:18][C:19]3([C:23]4[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=4)[CH2:22][CH2:21][CH2:20]3)=[CH:15][CH:16]=2)=[CH:7][C:3]=1[C:4](O)=[O:5].[NH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:43])[O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[N:13][C:14]([NH:17][CH2:18][C:19]3([C:23]4[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=4)[CH2:20][CH2:21][CH2:22]3)=[CH:15][CH:16]=2)=[CH:7][C:3]=1[C:4]([NH:30][CH2:31][CH2:32][NH:33][C:34](=[O:43])[O:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:5]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2794257Benzyl N-(2-aminoethyl)carbamateHCID 67451761HCID 67451761, compound

Product 1

HCID 67453273HCID 67453273, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 dram vial was added 2-fluoro-5-(6-((1-(3-fluoropyridin-2-yl)cyclobutyl)methylamino)pyridazin-3-yl)benzoic acid (320 mg, 0.8 mmol, 1.0 equiv), benzyl 2-aminoethylcarbamate (242 mg, 1.0 mmol, 1.3 equiv), HOBt (141 mg, 1.0 mmol, 1.3 equiv), EDC HCl (200 mg, 1.0 mmol, 1.3 equiv), DIPEA (550 μL, 3.8 equiv) and CH2Cl2 (5 mL). The reaction was stirred for 4 h and then concentrated and then purified using a silica gel column (50%-100% EtOAc/hexanes) to afford 230 mg (50%) of benzyl 2-(2-fluoro-5-(6-((1-(3-fluoropyridin-2-yl)cyclobutyl)methylamino)pyridazin-3-yl)benzamido)ethylcarbamate as a white foam.

Workup

  1. concentrationconcentrated
  2. custompurified

Sources & evidence

ORD record
ord-5f3884a359724ca3ad00164bbd947063
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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