Hydrochloric Acid → 1'-[(3-Phenyl-1-pyridin-2-yl-1H-thieno[2,3-c]pyrazol-5-yl)carbonyl]-6-(tetrazol-5-yl)spiro[chroman-2,4'-piperidin]-4-one

HRID 1096910Notes

Reaction equation

HRID 1096910 reaction equation
[C:1]1([C:7]2[C:8]3[CH:20]=[C:19]([C:21]([OH:23])=O)[S:18][C:9]=3[N:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH:25]1[CH2:30][CH2:29][C:28]2([CH2:39][C:38](=[O:40])[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[O:31]2)[CH2:27][CH2:26]1.CC[N:43]=[C:44]=[N:45]CCCN(C)C.C1C=CC2N(O)[N:59]=[N:58]C=2C=1.Cl>O.CCN(CC)CC.CN(C=O)C>[C:1]1([C:7]2[C:8]3[CH:20]=[C:19]([C:21]([N:25]4[CH2:30][CH2:29][C:28]5([CH2:39][C:38](=[O:40])[C:37]6[C:32](=[CH:33][CH:34]=[C:35]([C:44]7[NH:45][N:59]=[N:58][N:43]=7)[CH:36]=6)[O:31]5)[CH2:27][CH2:26]4)=[O:23])[S:18][C:9]=3[N:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2771097Spiro(1-benzopyran-2,4'-piperidin)-4(3H)-one--hydrogen chloride (1/1)HCID 667826543-phenyl-1-pyridin-2-yl-1H-thieno[2,3-c]pyrazole-5-carboxylic acid

Product 1

HCID 1785153791'-[(3-Phenyl-1-pyridin-2-yl-1H-thieno[2,3-c]pyrazol-5-yl)carbonyl]-6-(tetrazol-5-yl)spiro[chroman-2,4'-piperidin]-4-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

DMF (10 mL) and Et3N (1 mL) were added to 3-phenyl-1-pyridin-2-yl-1H-thieno[2,3-c]pyrazole-5-carboxylic acid (160 mg), 6-tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (190 mg), EDCI (120 mg) and HOBT (90 mg), heated at 50° C. and stirred overnight. This was further stirred at 110° C. for 1 hour, then restored to room temperature, diluted with water, and its pH was adjusted at 1.5 with 1 N HCl added thereto. The formed crystal was taken out through filtration, washed with water, n-hexane and water, and dried in vacuum at 60° C. to obtain the title compound as a pale brown power. 1H-NMR (400 MHz, DMSO-d6) δ: 8.62-8.57 (1H, m), 8.44 (1H, d, J=2.2 Hz), 8.26 (1H, dd, J=8.0, 2.2 Hz), 8.16-8.06 (4H, m), 7.92 (1H, s), 7.55 (2H, t, J=8.0 Hz), 7.50-7.45 (1H, m), 7.41-7.34 (2H, m), 4.30-4.20 (2H, br m), 3.53 (2H, s), 3.01 (2H, s), 2.12-2.04 (2H, br m), 1.95-1.84 (2H, br m). MS [M+H]+=589.

Workup

  1. stirringThis was further stirred at 110° C. for 1 hour
  2. customrestored to room temperature
  3. additionadded
  4. filtrationThe formed crystal was taken out through filtration
  5. washwashed with water, n-hexane and water
  6. customdried in vacuum at 60° C.

Sources & evidence

ORD record
ord-8e73cc04a28d4d7ebe30440c7bcc5a62
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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