Isopropylamine → 4-{3-(Cyanomethyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-2,5-difluoro-N-isopropylbenzamide

HRID 571477Notes

Reaction equation

Cl[C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:12])[CH:3]=1.[CH3:13][CH:14]([NH2:16])[CH3:15].Cl.Cl.C[Si](C)(C)CCOC[N:25]1[C:29]2[N:30]=[CH:31][N:32]=[C:33]([C:34]3[CH:35]=[N:36][N:37]([C:39]4([CH2:43][C:44]#[N:45])[CH2:42][NH:41][CH2:40]4)[CH:38]=3)[C:28]=2[CH:27]=[CH:26]1>>[C:44]([CH2:43][C:39]1([N:37]2[CH:38]=[C:34]([C:33]3[C:28]4[CH:27]=[CH:26][NH:25][C:29]=4[N:30]=[CH:31][N:32]=3)[CH:35]=[N:36]2)[CH2:42][N:41]([C:2]2[C:10]([F:11])=[CH:9][C:5]([C:6]([NH:16][CH:14]([CH3:15])[CH3:13])=[O:8])=[C:4]([F:12])[CH:3]=2)[CH2:40]1)#[N:45]

Participants

Reactant 3

HCID 6363Isopropylamine

HCID 27332744-Chloro-2,5-difluorobenzoic acid

HCID 67391464{3-[4-(7-{[2-(Trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile dihydrochloride

Product 1

HCID 711436104-{3-(Cyanomethyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-2,5-difluoro-N-isopropylbenzamide

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 3, Step 1-3 starting from 4-chloro-2,5-difluorobenzoic acid (Aldrich: Cat. #443824), 2-propanamine and {3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile dihydrochloride. LCMS (M+H)+: m/z=477.2. 1H NMR (400 MHz, DMSO-d6): δ 12.61 (s, 1H), 9.08 (s, 1H), 8.84 (s, 1H), 8.57 (s, 1H), 7.80 (m, 2H), 7.37 (dd, J=13.0, 7.0 Hz, 1H), 7.23 (m, 1H), 6.63 (dd, J=13.0, 8.0 Hz, 1H), 4.51 (d, J=9.0 Hz, 2H), 4.42 (d, J=9.0 Hz, 2H), 3.78 (s, 2H), 4.03 (m, 1H), 1.13 (d, J=6.5 Hz, 6H).

Workup

customThis compound was prepared

Sources & evidence

ORD record: ord-bb97af36145648e9a4b933de2a41d1b0
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023840B2

Reaction notes

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