Triethylamine → 4-({1-[4-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-amino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2093869Notes

Reaction equation

HRID 2093869 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]3[O:10][CH2:11][O:12][C:8]=3[C:7]=2[C:15]2[C:16]3[NH:23][CH:22]=[C:21]([C:24](O)=[O:25])[C:17]=3[N:18]=[CH:19][N:20]=2)[CH2:3][CH2:2]1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.[C:56]([O:60][C:61]([N:63]1[CH2:68][CH2:67][CH:66]([NH2:69])[CH2:65][CH2:64]1)=[O:62])([CH3:59])([CH3:58])[CH3:57]>ClCCl>[C:56]([O:60][C:61]([N:63]1[CH2:68][CH2:67][CH:66]([NH:69][C:24]([C:21]2[C:17]3[N:18]=[CH:19][N:20]=[C:15]([C:7]4[C:8]5[O:12][CH2:11][O:10][C:9]=5[CH:13]=[CH:14][C:6]=4[O:5][CH2:4][CH:1]4[CH2:3][CH2:2]4)[C:16]=3[NH:23][CH:22]=2)=[O:25])[CH2:65][CH2:64]1)=[O:62])([CH3:59])([CH3:57])[CH3:58]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 12682914-Amino-1-Boc-piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 668660154-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid

Product 1

HCID 668660774-({1-[4-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-amino)-piperidine-1-carboxylic acid tert-butyl esterYield 71.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(5-cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (3.53 g; 10.0 mmol) from example A67 in dry dichloromethane (50 mL) is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (12.0 mmol), triethylamine (15.0 mmol) and 1-hydroxybenzotriazole (10.0 mmol). The suspension is stirred at ambient temperature for one hour. To the resulting solution, 4-amino-piperidine-1-carboxylic acid tert-butyl ester (12.0 mmol) is added and stirring is continued overnight at ambient temperature. The reaction mixture is loaded onto a silica gel column and purified by flash chromatography using acetic acid ethyl ester/2-propanol (98:2 v/v). The eluate containing the product fraction is collected and evaporated. The product is triturated with n-hexane and dried in high vacuo at 50° C. to yield 3.85 g of the title compound as white solid.

Workup

  1. stirringstirring
  2. waitis continued overnight at ambient temperature
  3. custompurified by flash chromatography
  4. additionThe eluate containing the product fraction
  5. customis collected
  6. customevaporated
  7. customThe product is triturated with n-hexane
  8. customdried in high vacuo at 50° C.

Sources & evidence

ORD record
ord-c085f6b5254248e3aa2f3c2fa5a26246
Source dataset
uspto-grants-2013_05
Patent number
US08445501B2

Reaction notes

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