HOAt → HCID 44587862, compound

HRID 645498Notes

Reaction equation

HRID 645498 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([NH2:21])=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=2)[CH2:4][CH2:3]1.[C:22]([C:24]1[N:29]=[C:28]([NH:30][CH2:31][CH:32]2[CH2:39][CH2:38][C:35]3([CH2:37][CH2:36]3)[CH2:34][CH2:33]2)[C:27]([C:40](O)=[O:41])=[CH:26][N:25]=1)#[N:23].CCN=C=NCCCN(C)C.Cl.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([NH:21][C:40]([C:27]3[C:28]([NH:30][CH2:31][CH:32]4[CH2:39][CH2:38][C:35]5([CH2:37][CH2:36]5)[CH2:34][CH2:33]4)=[N:29][C:24]([C:22]#[N:23])=[N:25][CH:26]=3)=[O:41])=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 687052435-[(1-Methyl-4-piperidinyl)oxy][1,1′-biphenyl]-2-amineHCID 68706702HCID 68706702, compound

Product 1

HCID 44587862HCID 44587862, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(1-methylpiperidin-4-yloxy)biphenyl-2-ylamine (0.27 mmol, step 58.2) and 2-cyano-4-[(spiro[2.5]oct-6-ylmethyl)amino]pyrimidine-5-carboxylic acid (0.33 mmol) in DMF (2 mL) are added EDCI-HCl (0.54 mmol) and HOAt (0.54 mmol) at 0° C. After stirring at the ambient temperature overnight, the reaction mixture is purified by RP-HPLC to give the title compound as a white solid; 1H NMR (CDCl3), δ 0.18-0.21 (2H, m), 0.27-0.30 (2H, m), 0.90-0.94 (2H, m), 1.14-1.25 (2H, m), 1.58-1.78 (5H, m), 1.85-1.92 (2H, m), 2.02-2.06 (2H, m), 2.32 (3H, s), 2.70 (2H, br s), 3.41-3.44 (2H, t), 4.35 (1H, m), 6.89 (1H, d), 6.97 (1H, dd), 7.35-7.37 (2H, m), 7.45-7.52 (3H, m), 7.65 (1H, s), 7.92 (1H, s), 8.06 (1H, d), 8.90 (1H, s).

Workup

  1. customthe reaction mixture is purified by RP-HPLC

Sources & evidence

ORD record
ord-a97b5977d03c48278ec2f79c2f28d81a
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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