tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate → Pyridin-3-ylmethyl 4-(2-amino-5-(thiophen-2-yl)phenylcarbamoyl)phenylcarbamate

HRID 1907750Notes

Reaction equation

HRID 1907750 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13]C(=O)OC(C)(C)C.CN(C)[C@@H]1CCN(CC2C=CC(C(O)=O)=CC=2)C1.[N:39]1[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][O:46][C:47]([NH:49][C:50]2[CH:58]=[CH:57][C:53]([C:54](O)=[O:55])=[CH:52][CH:51]=2)=[O:48])[CH:40]=1>>[NH2:13][C:3]1[CH:4]=[CH:5][C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:7][C:2]=1[NH:1][C:54]([C:53]1[CH:52]=[CH:51][C:50]([NH:49][C:47](=[O:48])[O:46][CH2:45][C:41]2[CH:40]=[N:39][CH:44]=[CH:43][CH:42]=2)=[CH:58][CH:57]=1)=[O:55]

Participants

4

Reactant 3

HCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamateHCID 597373314-((Pyridin-3-ylmethoxy)carbonylamino)benzoic acidHCID 59737509(R)-4-((3-(Dimethylamino)pyrrolidin-1-yl)methyl)benzoic acid

Product 1

HCID 59737233Pyridin-3-ylmethyl 4-(2-amino-5-(thiophen-2-yl)phenylcarbamoyl)phenylcarbamateYield 31%

Procedure

Following the same procedure as described in Example 1, steps 6 and 7 (scheme 1), using compound 4 but substituting compounds 7 & 8 for compounds 281 & 282, the title compound 283 was obtained (step 2: 31% yield, step 3: 23% yield).

Sources & evidence

ORD record
ord-38158648330f4949b2263d53d7fbebfa
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

Loading…