Hydrochloric Acid → HCID 67540453, compound

HRID 1192301Notes

Reaction equation

HRID 1192301 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[NH:22][CH:21]=[CH:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.Cl.[NH:24]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@@H:25](C(O)=O)[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.O1CCOCC1>[C:40]([O:39][C:37](=[O:38])[NH:24][CH:25]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:15]3[NH:22][CH:21]=[CH:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:12][CH2:13]1)([CH3:43])([CH3:41])[CH3:42]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 67539894tert-Butyl 4-(5H-pyrrolo[3,2-d]pyrimidin-4-yl)piperazine-1-carboxylate

Product 1

HCID 67540453HCID 67540453, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(5H-Pyrrolo[3,2-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (43 mg, 0.14 mmol) in DCM (4 mL) was added HCl in Dioxane (4M, 1 mL). The mixture was stirred at room temperature for 4 hours. The solvent was removed and the residue was treated with TEA (2 mL), Boc-D-Phe(4-Cl)—OH (43 mg, 0.14 mmol), HOBT (30 mg, 0.222 mmol) and EDCI (41 mg, 0.214 mmol) in DCM (5 mL). The mixture was stirred at room temperature for 12 hours. The solvent was removed and the residue was subject to chromatography on silica gel to give product {1-(4-chlorobenzyl)-2-oxo-2-[4-(5H-pyrrolo[3,2-d]pyrimidin-4-yl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester (30 mg, 44%). 1H NMR (CDCl3, 400 Hz) δ 9.85 (s, 1H), 8.48 (s, 1H), 7.37 (s, 1H), 7.25-7.23 (d, J=8.4 Hz, 2H), 7.13-7.11 (d, J=8.4 Hz, 2H), 6.60 (s, 1H), 5.39-5.37 (d, J=8.8 Hz, 1H), 4.83-4.78 (m, 1H), 3.81-3.43 (m, 7H), 3.31-3.27 (m, 1H), 3.00-2.91 (m, 2H), 1.41 (s, 9H). MS (ESI+) [M+H]+ 485.

Workup

  1. customThe solvent was removed
  2. stirringThe mixture was stirred at room temperature for 12 hours
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-93f4fea7be6143b3b11c1a870af0d202
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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