Triethylamine → HCID 68541670, compound

HRID 1446707Notes

Reaction equation

HRID 1446707 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:38])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[N:23]4[CH:24]=[CH:25][C:26]([C:28]5[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=5)=[CH:27][C:22]4=[N:21][CH:20]=3)=[CH:15][C:14]=2[F:37])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:39]([O:43][C:44]([N:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1)=[O:45])([CH3:42])([CH3:41])[CH3:40].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[C:39]([O:43][C:44]([N:46]1[CH2:51][CH2:50][N:49]([C:32](=[O:33])[C:31]2[CH:35]=[CH:36][C:28]([C:26]3[CH:25]=[CH:24][N:23]4[C:19]([C:16]5[CH:17]=[CH:18][C:13]([NH:12][C:11]([NH:10][C:7]6[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[O:9][N:8]=6)=[O:38])=[C:14]([F:37])[CH:15]=5)=[CH:20][N:21]=[C:22]4[CH:27]=3)=[CH:29][CH:30]=2)[CH2:48][CH2:47]1)=[O:45])([CH3:42])([CH3:40])[CH3:41]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68546873HCID 68546873, compound

Product 1

HCID 68541670HCID 68541670, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 4-(3-{4-[3-(5-tert-Butyl-isoxazol-3-yl)-ureido]-3-fluoro-phenyl}-imidazo[1,2-a]pyridin-7-yl)-benzoic acid (2.00 g, 3.89 mmol), piperazine-1-carboxylic acid tert-butyl ester (1.09 g, 5.84 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.821 g, 4.28 mmol), triethylamine (1.63 mL, 11.68 mmol), and 1-hydroxybenzotriazole (0.579 g, 4.28 mmol) in DMF (50 mL). Stir at room temperature for 14 hours. Partition between ethyl acetate and 1 N NaOH, wash with aqueous saturated sodium chloride, dry over magnesium sulfate, filter, and concentrate. Triturate the resulting solid from CH2Cl2/hexanes, filter, and dry to give off-white solid as product (1.53 g, 58%). MS (ES), m/z 683 (M+1).

Workup

  1. customPartition between ethyl acetate and 1 N NaOH
  2. washwash with aqueous saturated sodium chloride
  3. dry with materialdry over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customTriturate the resulting solid from CH2Cl2/hexanes
  7. filtrationfilter
  8. customdry
  9. customto give off-white solid as product (1.53 g, 58%)

Sources & evidence

ORD record
ord-b11647124ccf4aa49303a149b6845318
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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