Water → Methyl 3-[[[1-(1-methylethyl)-4-piperidinyl]amino]carbonyl]-1H-indazole-5-carboxylate

HRID 902180Notes

Reaction equation

HRID 902180 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[C:14]([OH:16])=O)=[O:4].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.Cl.[CH:33]([N:36]1[CH2:41][CH2:40][CH:39]([NH2:42])[CH2:38][CH2:37]1)([CH3:35])[CH3:34].O>C(Cl)Cl.CCN(CC)CC>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[C:14](=[O:16])[NH:42][CH:39]1[CH2:40][CH2:41][N:36]([CH:33]([CH3:35])[CH3:34])[CH2:37][CH2:38]1)=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 230334601-Isopropylpiperidin-4-amine hydrochlorideHCID 690376921H-Indazole-3,5-dicarboxylic acid 5-methyl ester

Product 1

HCID 69033733Methyl 3-[[[1-(1-methylethyl)-4-piperidinyl]amino]carbonyl]-1H-indazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1 g 1H-Indazole-3,5-dicarboxylic acid 5-methyl ester in 8 mL DCM, 2.5 mL NEt3, 1.15 g BOP-Cl and 0.98 g 1-Isopropyl-piperidin-4-ylamine hydrochloride were added at RT. The mixture was stirred for 3 h. After addition of 20 mL of water the reaction mixture was extracted with DCM (3×50 mL). The combined organic layers were dried over MgSO4. After removal of the solvent under reduced pressure the crude product was used without further purification.

Workup

  1. extractionwas extracted with DCM (3×50 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customAfter removal of the solvent under reduced pressure the crude product
  4. customwas used without further purification

Sources & evidence

ORD record
ord-5b69aed7941f4294a7047df8dd8d62b6
Source dataset
uspto-grants-2008_04
Patent number
US07365088B2

Reaction notes

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