Hydrochloric Acid → HCID 178456628, compound

HRID 1096904Notes

Reaction equation

HRID 1096904 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:11]=[C:12]([C:13]([OH:15])=O)[C:7]=2[CH:6]=[N:5]1)[CH3:3].Cl.[NH:23]1[C:27]([C:28]2[CH:29]=[C:30]3[C:40](=[CH:41][CH:42]=2)[O:39][C:33]2([CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH2:32][C:31]3=[O:43])=[N:26][N:25]=[N:24]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl>O.CN(C=O)C>[CH3:3][CH:2]([N:4]1[C:8]2=[N:9][C:10]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:11][C:12]([C:13]([N:36]3[CH2:37][CH2:38][C:33]4([CH2:32][C:31](=[O:43])[C:30]5[C:40](=[CH:41][CH:42]=[C:28]([C:27]6[NH:26][N:25]=[N:24][N:23]=6)[CH:29]=5)[O:39]4)[CH2:34][CH2:35]3)=[O:15])=[C:7]2[CH:6]=[N:5]1)[CH3:1]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 25350531-(1-Methylethyl)-6-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidHCID 178479612HCID 178479612, compound

Product 1

HCID 178456628HCID 178456628, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

TEA (0.2 mL) was added to a DMF suspension (2 mL) of 1-(1-methylethyl)-6-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid, 6-(tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride, EDCI and HOBT.H2O, heated at 80° C. and stirred for 2 hours. This was cooled to room temperature, iced water was added thereto, and its pH was adjusted to 2.5 with 1 N HCl solution added thereto. The resulting 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: 8.34 (1H, d, J=2.2 Hz), 8.26-8.21 (2H, m), 8.19 (1H, s), 8.19 (1H, dd, J=8.4, 2.6 Hz), 7.82 (1H, s), 7.58-7.47 (3H, m), 7.20 (1H, d, J=8.4 Hz), 5.33 (1H, sept, J=6.8 Hz), 4.45-4.30 (1H, m), 3.70-3.00 (3H, m), 2.95 (2H, s), 2.20-1.70 (4H, m), 1.55 (6H, d, J=6.8 Hz). MS [M+H]+=549.

Workup

  1. additionadded
  2. filtrationThe resulting crystal was taken out through filtration
  3. washwashed with water
  4. washwashed with Et2O
  5. customdried in vacuum at 70° C.

Sources & evidence

ORD record
ord-de9ebda2ee08404f8f2ffce51b59b8d6
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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