Sodium Carbonate → (R)-tert-Butyl 3-(4-chlorophenyl)-1-(4-(3-methyl-5-phenyl-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-1-oxopropan-2-ylcarbamate

HRID 79606Notes

Reaction equation

HRID 79606 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:9]=2[N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[NH:4][CH:3]=1.[C:23]([O:27][C:28]([NH:30][C@H:31]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)[C:32](O)=[O:33])=[O:29])([CH3:26])([CH3:25])[CH3:24].C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([CH2:35][C@@H:31]([NH:30][C:28](=[O:29])[O:27][C:23]([CH3:25])([CH3:24])[CH3:26])[C:32]([N:14]2[CH2:13][CH2:12][N:11]([C:9]3[C:8]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:7][N:6]=[C:5]4[NH:4][CH:3]=[C:2]([CH3:1])[C:10]=34)[CH2:16][CH2:15]2)=[O:33])=[CH:37][CH:38]=1

Participants

8

Reactant 6

HCID 10340Sodium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 687614063-Methyl-5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 68761327(R)-tert-Butyl 3-(4-chlorophenyl)-1-(4-(3-methyl-5-phenyl-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-1-oxopropan-2-ylcarbamateYield 38.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methyl-5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine (0.050 g, 0.14 mmol, see Example 15), (R)-2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoic acid (0.0451 g, 0.151 mmol), HOBT-H2O (0.0293 g, 0.192 mmol) and EDCI (0.0341 g, 0.178 mmol) were placed in DCM (5 mL) at room temperature. DIEA (d 0.742; 0.119 mL, 0.684 mmol) was then added, and the reaction was stirred for 5 hours. The reaction was then poured into saturated Na2CO3 and extracted into DCM. The reaction was then dried, filtered, concentrated, and purified (500:5 DCM:MeOH) to give (R)-tert-butyl 3-(4-chlorophenyl)-1-(4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-1-oxopropan-2-ylcarbamate (0.030 g, 38.1% yield).

Workup

  1. extractionextracted into DCM
  2. customThe reaction was then dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified (500:5 DCM:MeOH)

Sources & evidence

ORD record
ord-e3a29bc7330b4758a8a7e12b2dca6b17
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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