Methanol → HCID 178425295, compound

HRID 1047837Notes

Reaction equation

HRID 1047837 reaction equation
[CH:1]1([O:5][C:6]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:7]=2[C:8]([NH:10][C:11]2([C:20](O)=[O:21])[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)=[O:9])[CH2:4][CH2:3][CH2:2]1.[NH2:28][C:29]1[NH:33][N:32]=[N:31][N:30]=1.Cl.CN(C)CCCN=C=NCC.CO>CN(C)C1C=CN=CC=1.C(Cl)Cl>[NH:30]1[C:29]([NH:28][C:20]([C:11]2([NH:10][C:8](=[O:9])[C:7]3[CH:23]=[CH:24][CH:25]=[C:26]([CH3:27])[C:6]=3[O:5][CH:1]3[CH2:4][CH2:3][CH2:2]3)[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)=[O:21])=[N:33][N:32]=[N:31]1

Participants

7

Reactant 4

HCID 887MethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 251602822-(2-Cyclobutoxy-3-methyl-benzoylamino)-indan-2-carboxylic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178425295HCID 178425295, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A 40 mL tube is charged with 2-[(2-cyclobutoxy-3-methyl-benzoyl)-amino]-indan-2-carboxylic acid (323 mg, 0.884 mmol) and dry DCM (7 mL). A stirring bar is added and stirring is initiated. 5-Amino-1H-tetrazole (113 mg, 1.33 mmol) is added. To the resultant suspension, N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (170 mg, 0.88 mmol) and 4-dimethylaminopyridine (108 mg, 0.88 mmol) is added. After 11½ days, tlc analysis (silica, 10% MeOH in DCM) indicates that the starting acid had been consumed. The reaction mixture is diluted with EtOAc (50 mL), transferred to an Erlenmeyer flask containing saturated aqueous ammonium chloride (50 mL). This mixture is allowed to stir. After 16 h of stirring, this mixture contained a white solid that is collected by suction filtration and washed with water (2×25 mL). Air drying gives 0.26 g of white powder.

Workup

  1. additionA stirring bar is added
  2. waitAfter 11½ days
  3. customhad been consumed
  4. additionThe reaction mixture is diluted with EtOAc (50 mL)
  5. customtransferred to an Erlenmeyer flask
  6. additioncontaining saturated aqueous ammonium chloride (50 mL)
  7. stirringto stir
  8. stirringAfter 16 h of stirring
  9. filtrationthat is collected by suction filtration
  10. washwashed with water (2×25 mL)
  11. customAir drying

Sources & evidence

ORD record
ord-5e8583769390482f9fd0d8e95938e91d
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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