Hydrochloric Acid → HCID 178433902, compound

HRID 1096911Notes

Reaction equation

HRID 1096911 reaction equation
Cl.[NH:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:19](=[CH:20][CH:21]=2)[O:18][C:12]2([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH2:11][C:10]3=[O:22])=[N:5][N:4]=[N:3]1.[CH3:23][C:24]1[C:25]2[CH:37]=[C:36]([C:38](O)=[O:39])[S:35][C:26]=2[N:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[N:28]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl>CCN(CC)CC.CN(C=O)C.O.CCOCC.C(Cl)(Cl)Cl>[CH3:23][C:24]1[C:25]2[CH:37]=[C:36]([C:38]([N:15]3[CH2:16][CH2:17][C:12]4([CH2:11][C:10](=[O:22])[C:9]5[C:19](=[CH:20][CH:21]=[C:7]([C:6]6[NH:2][N:3]=[N:4][N:5]=6)[CH:8]=5)[O:18]4)[CH2:13][CH2:14]3)=[O:39])[S:35][C:26]=2[N:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[N:28]=1

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 43328339HCID 43328339, compoundHCID 178479612HCID 178479612, compound

Product 1

HCID 178433902HCID 178433902, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

6-(Tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (232 mg), 3-methyl-1-pyridin-2-yl-1H-thieno[2,3-c]pyrazole-5-carboxylic acid (155 mg), EDCI (153 mg) and HOBT (122 mg) were suspended in Et3N (1 mL) and DMF (8 mL). The suspension was stirred at 80° C. for 1.5 hours under heat, then cooled to room temperature, and chloroform (1.8 mL) was added thereto. Its pH was adjusted at 2.5 with 1 N HCl added thereto, and this was diluted with water, and Et2O was added thereto. The formed crystal was taken out through filtration, washed with water and Et2O—CHCl3, and dried in vacuum to obtain the title compound as a pale yellow powder. 1H-NMR (400 MHz, DMSO-d6): δ 8.53 (1H, d, J=4.4 Hz), 8.44 (1H, s), 8.25 (1H, d, J=8.5 Hz), 8.01 (1H, t, J=7.8 Hz), 7.90 (1H, d, J=8.5 Hz), 7.61 (1H, s), 7.37 (1H, d, J=8.8 Hz), 7.31 (1H, t, J=5.9 Hz), 6.44 (2H, s), 4.20 (2H, d, J=12.9 Hz), 3.48 (2H, br s), 2.52 (3H, s), 2.06 (2H, d, J=13.7 Hz), 1.94-1.81 (2H, m). MS [M+H]+=527.

Workup

  1. temperatureunder heat
  2. temperaturecooled to room temperature
  3. additionadded
  4. additionwas added
  5. filtrationThe formed crystal was taken out through filtration
  6. washwashed with water and Et2O—CHCl3
  7. customdried in vacuum

Sources & evidence

ORD record
ord-d2c4222632cb4b33bf244bf716a0b18a
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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