3-Chloro-2-fluoroaniline → HCID 68519314, compound

HRID 1948940Notes

Reaction equation

HRID 1948940 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:26][CH3:27])=[C:9]([O:12][CH2:13][CH:14]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]3)[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:28][C:29]1[C:30]([F:36])=[C:31]([CH:33]=[CH:34][CH:35]=1)[NH2:32]>>[ClH:1].[Cl:28][C:29]1[C:30]([F:36])=[C:31]([CH:33]=[CH:34][CH:35]=1)[NH:32][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:26][CH3:27])=[C:9]([O:12][CH2:13][CH:14]3[CH2:18][CH2:17][NH:16][CH2:15]3)[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 750143-Chloro-2-fluoroanilineHCID 866008284-Chloro-7-methoxy-6-{[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]methoxy}quinazoline

Product 1

HCID 68519314HCID 68519314, compoundYield 100%

Procedure

4-chloro-7-methoxy-6-{[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]methoxy}quinazoline (4.5 g) was reacted with 3-chloro-2 fluoroaniline to give 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-(pyrrolidin-3-ylmethoxy)quinazoline hydrochloride (5.45 g, 100%); 1H NMR Spectrum: (DMSO d6) 1.71-1.85 (m, 1H); 2.10-2.22 (m, 1H); 2.81-2.91 (m, 1H); 2.97-3.07 (m, 1H); 3.11-3.22 (m, 1H); 3.24-3.33 (m, 1H); 3.35-3.46 (m, 1H); 4.00 (s, 3H); 4.28-4.34 (m, 2H); 7.31-7.37 (m, 1H); 7.43 (s, 1H); 7.49-7.54 (m, 1H); 7.59-7.64 (m, 1H); 8.60 (s, 1H); 8.80 (s, 1H); 9.32 (bs, 2H); 12.05 (bs, 1H); Mass Spectrum: (M−H)− 401.

Sources & evidence

ORD record
ord-f656575394014aeaa7d5ee72a1c4b07d
Source dataset
uspto-grants-2013_03
Patent number
US08399667B2

Reaction notes

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