Morpholine → HCID 67297999, compound

HRID 1520345Notes

Reaction equation

C(NC1C(C)=CC(OC)=CC=1C(N)=O)(=O)C1C=CC=CC=1.NC1C(C)=CC(OC)=CC=1C(N)=O.[Cl:35][C:36]1[CH:37]=[C:38]([NH:43][C:44]2[C:53]3[C:48](=[CH:49][CH:50]=[C:51]([CH2:54][CH2:55][CH2:56][C:57]([OH:59])=O)[CH:52]=3)[N:47]=[C:46]([C:60]3[CH:61]=[N:62][CH:63]=[CH:64][CH:65]=3)[N:45]=2)[CH:39]=[CH:40][C:41]=1[F:42].[NH:66]1[CH2:71][CH2:70][O:69][CH2:68][CH2:67]1>>[Cl:35][C:36]1[CH:37]=[C:38]([NH:43][C:44]2[C:53]3[C:48](=[CH:49][CH:50]=[C:51]([CH2:54][CH2:55][CH2:56][C:57]([N:66]4[CH2:71][CH2:70][O:69][CH2:68][CH2:67]4)=[O:59])[CH:52]=3)[N:47]=[C:46]([C:60]3[CH:61]=[N:62][CH:63]=[CH:64][CH:65]=3)[N:45]=2)[CH:39]=[CH:40][C:41]=1[F:42]

Participants

Reactant 4

HCID 8083Morpholine

HCID 67298040HCID 67298040, compound

HCID 67298121HCID 67298121, compound

HCID 67298161HCID 67298161, compound

Product 1

HCID 67297999HCID 67297999, compoundYield 40%

Procedure

4-(4-(3-chloro-4-fluorophenylamino)-2-(pyridin-3-yl) quinazolin-6-yl)-1-morpholinobutan-1-one was prepared in a manner analogous to that described for 2-benzamido-5-methoxy-3-methylbenzamide in Method D, replacing nicotinic acid and 2-amino-5-methoxy-3-methylbenzamide with 4-(4-(3-chloro-4-fluorophenylamino)-2-(pyridin-3-yl)quinazolin-6-yl) butanoic acid and morpholine to give 32 mg of xxxv-a in a 40% yield as a beige solid. LCMS m/z=506.2, 508.1 (M+1) (Method 1) (retention time=1.85 min). 1H NMR (400 MHz, DMSO-d6): δ 10.04 (s, 1H), 9.52 (d, J=1.6 Hz, 1H), 8.69-8.65 (m, 2H), 8.39-8.38 (m, 1H), 8.27 (dd, J=6.8, 2.8 Hz, 1H), 7.94-7.90 (m, 1H), 7.86-7.84 (m, 1H), 7.80-7.77 (m, 1H), 7.57-7.52 (m, 2H), 3.56-3.53 (m, 4H), 3.46-3.41 (m, 4H), 2.85 (t, J=8.0 Hz, 2H), 2.40 (t, J=7.6 Hz, 2H), 1.97 (t, J=7.6 Hz, 2H).

Workup

customto give 32 mg of xxxv-a in a 40% yield as a beige solid

Sources & evidence

ORD record: ord-bc785a764b214d30b8b31b46fbb4768d
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073890B2

Reaction notes

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