4-(Piperazin-1-yl)-1H-pyrrolo[2,3-d]pyrimidine dihydrochloride → 3-Amino-2-(4-bromo-2-fluoro-benzyl)-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one dihydrochloride

HRID 1192377Notes

Reaction equation

HRID 1192377 reaction equation
[ClH:1].Cl.[N:3]1([C:9]2[C:10]3[CH:17]=[CH:16][NH:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[Br:18][C:19]1[CH:38]=[CH:37][C:22]([CH2:23][CH:24]([CH2:28][NH:29]C(OC(C)(C)C)=O)[C:25](O)=[O:26])=[C:21]([F:39])[CH:20]=1>>[ClH:1].[ClH:1].[NH2:29][CH2:28][CH:24]([CH2:23][C:22]1[CH:37]=[CH:38][C:19]([Br:18])=[CH:20][C:21]=1[F:39])[C:25]([N:6]1[CH2:5][CH2:4][N:3]([C:9]2[C:10]3[CH:17]=[CH:16][NH:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH2:8][CH2:7]1)=[O:26]

Participants

3

Reactant 2

HCID 675378564-(Piperazin-1-yl)-1H-pyrrolo[2,3-d]pyrimidine dihydrochlorideHCID 675398202-(4-Bromo-2-fluoro-benzyl)-3-tert-butoxycarbonylamino-propionic acid

Product 1

HCID 675390613-Amino-2-(4-bromo-2-fluoro-benzyl)-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one dihydrochloride

Procedure

3-Amino-2-(4-bromo-2-fluoro-benzyl)-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one dihydrochloride was prepared by substituting 5-piperazin-1-yl-1H-indazole with 4-Piperazin-1-yl-7H-pyrrolo[2,3-d]pyrimidine dihydrochloride and substituting (D)-Boc-4-chlorophenylalanine with 2-(4-Bromo-2-fluoro-benzyl)-3-tert-butoxycarbonylamino-propionic acid in Example 34, Step 2, then removing the Boc protecting group as described in Example 34, Step 3. 1H NMR (CD3OD, 400 MHz) δ 8.37 (s, 1H), 7.40 (d, J=3.6 Hz, 1H), 7.36 (m, 1H), 7.31 (m, 1H), 7.24 (t, J=8.0 Hz, 1H), 6.95 (d, J=3.6 Hz, 1H), 4.14 (m, 2H), 4.02 (m, 1H), 3.87 (m, 4H), 3.55 (m, 2H), 3.34 (m, 1H), 3.11 (m, 1H), 2.98 (m, 2H). LCMS (APCI+) m/z 461, 463 [M+H]+; Rt=1.79 min.

Workup

  1. customremoving the Boc protecting group

Sources & evidence

ORD record
ord-fc86a5a70df64b4baad06e1ffc794698
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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