HCID 69676500, compound → HCID 69676417, compound

HRID 919631Notes

Reaction equation

ClC1C=C(NCC(N2CCC3CCN(C4C5C=CNC=5N=CN=4)C3C2)=O)C=C(Cl)C=1.[CH:31]1([C@:34]([NH:58][C:59]2[CH:64]=[C:63]([Cl:65])[CH:62]=[C:61]([Cl:66])[CH:60]=2)(CCC)[C:35]([N:37]2[CH2:42][CH2:41][CH:40]3[CH2:43][CH2:44][N:45]([C:46]4[C:47]5[CH:54]=[CH:53][NH:52][C:48]=5[N:49]=[CH:50][N:51]=4)[CH:39]3[CH2:38]2)=[O:36])[CH2:33][CH2:32]1>>[N:49]1[C:48]2[NH:52][CH:53]=[CH:54][C:47]=2[C:46]([N:45]2[CH:39]3[CH2:38][N:37]([C:35](=[O:36])[C@H:34]([NH:58][C:59]4[CH:60]=[C:61]([Cl:66])[CH:62]=[C:63]([Cl:65])[CH:64]=4)[CH:31]4[CH2:32][CH2:33]4)[CH2:42][CH2:41][CH:40]3[CH2:43][CH2:44]2)=[N:51][CH:50]=1

Participants

Reactant 2

HCID 69676500HCID 69676500, compound

HCID 118890535HCID 118890535, compound

Product 1

HCID 69676417HCID 69676417, compound

Procedure

A similar procedure was used as described for the synthesis 2-(3,5-dichloro-phenylamino)-1-[1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-octahydro-pyrrolo[2,3-c]pyridin-6-yl]-ethanone using (2R)-2-cyclopropyl-(3,5-dichlorophenylamino)-1-[1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-octahydro-pyrrolo[2,3-c]pyridin-6-yl]pentan-1-one in place of 2-(3,5-dichloro-phenylamino)-1-[1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-octahydro-pyrrolo[2,3-c]pyridin-6-yl]-ethanone. 1H NMR (400 MHz, DMSO-d6) δ=11.37 (br. s., 1H), 7.98-7.75 (m, 1H), 6.89 (br. s., 1H), 6.59-6.14 (m, 3H), 5.52 (s, 1H), 4.56-4.27 (m, 1H), 4.03 (br. s., 2H), 3.83-3.37 (m, 3H), 2.13-1.91 (m, 2H), 1.91-1.38 (m, 3H), 1.04-0.80 (m, 2H), 0.35-−0.25 (m, 4H). LC/MS (m/z): calcd. For C24H26Cl2N6O (M+1H) 485. found 485.

Sources & evidence

ORD record: ord-b72e635df8d4459dbd4bd663d8821505
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273028B2

Reaction notes

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