Trifluoroacetic acid → HCID 178520665, compound

HRID 34164Notes

Reaction equation

HRID 34164 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13])[N:8]=[CH:7][N:6]=[C:5]2[NH:19][CH:20]([C:26]1[N:30](C(OC(C)(C)C)=O)[C:29]2[CH:38]=[CH:39][C:40]([Cl:42])=[CH:41][C:28]=2[N:27]=1)[CH2:21][CH2:22][C:23](O)=[O:24].CN(C(ON1N=[N:58][C:53]2[CH:54]=[CH:55][CH:56]=[CH:57]C1=2)=[N+](C)C)C.[B-](F)(F)(F)F.FC(F)(F)C(O)=O.C(#[N:74])C.O1CCCC1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1)=[O:13])[N:8]=[CH:7][N:6]=[C:5]2[NH:19][CH:20]([C:26]1[NH:30][C:29]2[CH:38]=[CH:39][C:40]([Cl:42])=[CH:41][C:28]=2[N:27]=1)[CH2:21][CH2:22][C:23]([NH:74][CH:53]1[CH2:54][CH2:55][CH2:56][CH2:57][NH:58]1)=[O:24]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22177404Acetonitrile tetrahydrofuranHCID 689384896-chloro-4-[1-(1-tert.-butyloxycarbonyl-5-chloro-1H-benzimidazol-2-yl)-3-hydroxycarbonyl-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline

Product 1

HCID 178520665HCID 178520665, compound

Procedure

Prepared analogously to Example 61 from 6-chloro-4-[1-(1-tert.-butyloxycarbonyl-5-chloro-1H-benzimidazol-2-yl)-3-hydroxycarbonyl-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline and 2-amino-i-tert.-butyloxycarbonyl-piperidine with TBTU in acetonitrile/tetrahydrofuran and subsequent reaction with trifluoroacetic acid.

Sources & evidence

ORD record
ord-62e8b4a43f914e048126ebfaec89855b
Source dataset
uspto-grants-2008_09
Patent number
US07429597B2

Reaction notes

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