Hydrochloric Acid → HCID 178515378, compound

HRID 1096906Notes

Reaction equation

HRID 1096906 reaction equation
[CH:1]1([C:4]2[C:5]3[CH:17]=[C:16]([C:18](O)=[O:19])[S:15][C:6]=3[N:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=3)[N:8]=2)[CH2:3][CH2:2]1.Cl.[NH:22]1[C:26]([C:27]2[CH:28]=[C:29]3[C:39](=[CH:40][CH:41]=2)[O:38][C:32]2([CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH2:31][C:30]3=[O:42])=[N:25][N:24]=[N:23]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl>O.CN(C=O)C>[CH:1]1([C:4]2[C:5]3[CH:17]=[C:16]([C:18]([N:35]4[CH2:36][CH2:37][C:32]5([CH2:31][C:30](=[O:42])[C:29]6[C:39](=[CH:40][CH:41]=[C:27]([C:26]7[NH:25][N:24]=[N:23][N:22]=7)[CH:28]=6)[O:38]5)[CH2:33][CH2:34]4)=[O:19])[S:15][C:6]=3[N:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=3)[N:8]=2)[CH2:2][CH2:3]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 63353457HCID 63353457, compoundHCID 178479612HCID 178479612, compound

Product 1

HCID 178515378HCID 178515378, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

DMF (5 mL) and TEA (0.2 mL) were added to 3-cyclopropyl-1-pyridin-2-yl-1H-thieno[2,3-c]pyrazole-5-carboxylic acid (143 mg), 6-(tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (177 mg), EDCI (119 mg) and HOBT (90 mg), heated at 80° C. and stirred for 2 hours. This was cooled to room temperature, iced water was added to it, and its pH was adjusted at 2.5 with 1 N HCl added thereto. The formed crystal was taken out through filtration, washed with water, washed with Et2O and dried in vacuum at 70° C. to obtain the title compound as a pale brown powder. 1H-NMR (400 MHz, DMSO-d6) δ: 8.54-8.51 (1H, br m), 8.43 (1H, d, J=2.2 Hz), 8.25 (1H, dd, J=8.3, 2.2 Hz), 8.03-7.97 (1H, m), 7.88 (1H, d, J=8.3 Hz), 7.51 (1H, s), 7.36-7.27 (2H, m), 4.24-4.14 (2H, br m), 3.4-3.6 (2H, br m), 3.00 (2H, s), 2.31-2.22 (1H, m), 2.10-2.02 (2H, br m), 1.93-1.81 (2H, br m), 1.11-1.04 (4H, m). MS [M+H]+=553.

Workup

  1. temperatureThis was cooled to room temperature
  2. additionadded
  3. filtrationThe formed crystal was taken out through filtration
  4. washwashed with water
  5. washwashed with Et2O
  6. customdried in vacuum at 70° C.

Sources & evidence

ORD record
ord-004b6c8def924b60978759b9aa048a8a
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

Loading…